Category: 10534-59-5

10534-59-5, Tetrabutylammonium acetate is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solution of (25,5 ?)-6-benzyloxy-N’-{ [5-(2-tert- butyldimethysilanyloxyethyl)- lH-tetrazol- l-yl]acetyl}-7-oxo- l,6-diazabicyclo[3.2.1]octane-2- carbohydrazide (8 g, 14.3 mmol) in dimethylformamide (40 ml) and dichloromethane (40 ml) was added 10% Pd/C(50% wet basis) 2.4 g at 25- 30 C. The H2 gas was bubbled through the reaction mixture under stirring. The progress of reaction was monitored by TLC (chloroform: methanol, 9: 1). The catalyst was removed by filtration on celite bed and washed with mixture of dichloromethane and dimethylformamide (1 : 1, 2×20 ml). The filtrate was concentrated under reduced pressure yielded (25,5 ?)-6-hydoxy-N’-{ [5-(2-tert-butyldimethysilanyloxyethyl)- lH- tetrazol- l-yl]acetyl}-7-oxo- l,6-diazabicyclo[3.2.1]octane-2-carbohydrazide (6.6 g, c.a 100% yield used for next reaction as such). The product (25,5 ?)-6-hydoxy-N’-{ [5-(2-tert- butyldimethysilanyloxyethyl)- lH-tetrazol- l-yl]acetyl}-7-oxo- l,6-diazabicyclo[3.2.1]octane-2- carbohydrazide (6.6 g, 14.3 mmol) thus obtained was dissolved in dimethylformamide (40 ml) was added dimethylformamide sulfur trioxide complex (2.63 g, 17.20 mmol) in argon atmosphere at 0C under stirring. The progress of reaction was monitored by TLC (chloroform: methanol, 9: 1). After completion of the reaction added a solution of tetra-butyl ammonium acetate (5.18 g, 17.20 mmol) dissolved in water (18 ml) at 25-30C. The reaction mixture was stirred for 3 hours and concentrated under reduced pressure. The residue obtained was taken in dichloromethane (80 ml) and washed with water (2×40 ml). The organic extract was dried on anhydrous sodium sulfate and concentrated to yield crude tetrabutylammonium salt of (2S,5 ?)- V-{ [5-(2-tert- butyldimethysilanyloxyethyl)- lH-tetrazol- l-yl]acetyl}-7-oxo-6-sulfooxy- l,6-diazabicyclo[3.2.1] octane-2-carbohydrazide. This material was purified by column chromatography (silica gel 100-200 mesh size) using chloroform: methanol as an eluent. The fractions containing the product obtained at 5% methanol in chloroform. The pure fractions were combined and concentrated to get 7.5 g of tetrabutylammonium salt of (25,5 ?)-N’-{ [5-(2-tert-butyldimethysilanyloxyethyl)- lH-tetrazol- l- yl]acetyl}-7-oxo-6-sulfooxy- l,6-diazabicyclo[3.2.1]octane-2-carbohydrazide as off-white foam solid in 66% yield.

10534-59-5, As the paragraph descriping shows that 10534-59-5 is playing an increasingly important role.

Reference£º
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

10534-59-5, Tetrabutylammonium acetate is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3: Preparation of tert-butyl-(35)-3-[({[25,5R)-6-(sulfooxy)-7-oxo-l,6- diazabicylco[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidine-l-carboxylate, tetrabutyl ammonium salt (VI): To a stirred solution of ieri-butyl(35)-3-[({ [25,5i?)-6-hydroxy-7-oxo-l,6- diazabicylco[3.2.1]oct-2-yl]carbonyl}amino)oxy]pyrrolidine-l-carboxylate (V) (8.04 g, 0.0217 mol) in dimethylformamide (50 ml), was added sulfur trioxide dimethyl formamide complex (3.98 g, 0.0260 mol) in one portion, at about 10C. The stirring was continued further for 30 minute and then the reaction mixture was allowed to warm to room temperature. After 2 hour, a solution of tetrabutylammonium acetate (7.83 g, 0.0260 mol) in water (25.8 ml) was added to the resulting reaction mass under stirring. After additional 2 hour of stirring, the solvent from the reaction mixture was evaporated under reduced pressure to obtain an oily residue. The oily mass was co-evaporated with xylene (2 x 20 ml) to obtain thick mass. This mass was partitioned between dichloromethane (100 ml) and water (100 ml). The organic layer was separated and the aqueous layer re-extracted with dichloromethane (50 ml). The combined organic extracts were washed with water (3 x 50 ml), dried over anhydrous sodium sulphate and the solvent evaporated under reduced pressure. The residual oily mass was triturated with ether (3 x 50 ml), each time the ether layer was decanted and finally the residue was concentrated under reduced pressure to obtain 11.3 g of tert-butyl(3S)-3-[({ [2S,5R)-6- (sulfooxy)-7-oxo-l,6-diazabicylco[3.2.1]oct-2-yl]carbonyl}amino)oxy] pyrrolidine- 1- carboxylate, tetrabutylammonium salt (VI), as a white foam, in 75 % yield. Analysis: Mass: 449.3 (M-l, without TBA); for Molecular weight of 691.94 and Molecular formula of C32H61N5O9S; and 1H NMR (400MHz, CDC13): 59.14-9.10 (d, 1H), 4.63 (s, 1H), 4.35 (s, 1H), 3.94- 3.92 (d, 1H), 3.66-3.35 (m, 5H), 3.29-3.27 (m, 8H), 2.83-2.80 (d, 1H), 2.35-2.17 (m, 3H), 1.98-1.87 (m, 2H), 1.73 (m, 1H), 1.70-1.62 (m, 8H), 1.49-1.40 (m, 17H), 1.02-0.99 (t, 12H).

10534-59-5, As the paragraph descriping shows that 10534-59-5 is playing an increasingly important role.

Reference£º
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; BIRAJDAR, Satish; DOND, Bharat; PATIL, Vijaykumar Jagdishwar; PATEL, Mahesh Vithalbhai; WO2015/110886; (2015); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10534-59-5,Tetrabutylammonium acetate,as a common compound, the synthetic route is as follows.

To a solution of (25,5 ?)-6- (benzyloxy)-7-oxo-N-[2-(2H-l,2,3-triazol-2-yl)ethoxy]-l,6-diazabicyclo[3.2.1]octane-2- carboxamide (4 g, 10.3 mmol, upper spot as per thin layer chromatography in Step 3) in dimethylformamide (20 ml) and dichloromethane (20 ml) was added palladium over carbon (10%, 1.0 g) under nitrogen atmosphere. The reaction mixture was flushed with hydrogen gas and stirred for 3 hour under hydrogen pressure (55 psi). The progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (9: 1) as solvent system. After complete conversion, the reaction mixture was filtered through celite bed and washed with a mixture of dichloromethane and dimethylformamide (20 ml, 1: 1). The collected filtrate was evaporated under reduced pressure to dryness. The intermediate thus obtained was dissolved into dimethylformamide (20 ml) and dimethylformamide sulfur trioxide complex (2.4 g, 15.6 mmol) was added under stirring at 0 C. The reaction mixture was allowed to attain ambient temperature and stirred further for 1 hour. The completion of reaction was monitored by performing thin layer chromatography using mixture of chloroform and methanol as solvent system. After complete conversion, the reaction mixture was cooled to 0C and then a solution of tetra butyl ammonium acetate (5 g, 16.5 mmol) in water (17 ml) was slowly added under stirring. After 1 hour, the reaction mixture was concentrated to dryness in vacuum and co-evaporated with xylene (2×30 ml) to dimethylformamide free mass. To this concentrated mass, water (40 ml) was added and then extraction with dichloromethane was carried (2×40 ml). The collective organic layer was dried on anhydrous sodium sulfate and concentrated to dryness to provide 8.5 g of crude compound. It was purified using column chromatography (silcagel 60- 120) by using mixture of dichloromethane and methanol as an eluent. The pure compound was isolated at 5% concentration of methanol in dichloromethane; the collective fractions were collected and evaporated to obtain 3.5 g of tetrabutyl ammonium salt of (25,5 ?)-7-oxo-6-(sulfooxy)-N-[2-(2H- l,2,3-triazol-2-yl)ethoxy]- l,6-diazabicyclo[3.2.1]octane- 2-carboxamide in 55% yield. Analysis: Mass: 375.2 (M- l, for free acid) for Molecular weight: 617 and Molecular formula: C27H5iN707S., 10534-59-5

The synthetic route of 10534-59-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10534-59-5,Tetrabutylammonium acetate,as a common compound, the synthetic route is as follows.

To a stirred solution of 2,4 dimethoxy benzaldehyde (0.542 g, 3.3 mmol) in tetrahydrofuran (10 ml.), was added N, N-diisopropyl ethyl amine (1.0 g, 7.0 mmol) followed by the addition of (25,5 ?)-N-(2-hydrazino-2-oxoethyl)-7-oxo-6-(sulfooxy)- l,6-diazabicyclo [3.2.1 ]octane-2- carboxamide (1 g, 3.0mmol) at 25C. The reaction mixture was stirred for 16 hours and to the resulting mixture was added a solution of tetrabutylammonium acetate (0.3 g, 3.0 mmol) in tetrahydrofuran (10 ml.) and stirring continued further for 24 hours. The solvent was evaporated under reduced pressure and the residue was taken up in dichloro methane (20 ml) and washed with 10% aqueous potassium hydrogen sulfate solution (3 ml x 2) and finally organic layer was washed with water (5 ml). The organic layer was separated and dried over anhydrous sodium sulfate and evaporated under reduced pressure to yield a semi solid residue. This was purified by column chromatography over silica-gel (60- 120 mesh) by eluting with mixture of methanol in dichloro methane (5: 95). The combined fractions were evaporated under reduced pressure to obtain 1.1 g of tetrabutylammonium salt of (25,5 ?)-N-{2-[(2E,Z)-2-(2,4-dimethoxybenzylidenehydrazino]-2-oxoethyl}-7-oxo-6-(sulfooxy)- l,6- diazabicyclo[3.2.1]octane-2-carboxamide as a white solid in 51%

10534-59-5, 10534-59-5 Tetrabutylammonium acetate 82707, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; WOCKHARDT LIMITED; PATIL, Vijaykumar Jagdishwar; TADIPARTHI, Ravikumar; LOGANANTHAN, Velupillai; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; PAWAR, Mangesh; PATEL, Piyush Ambalal; JOSHI, Prashant Ratnakar; PATEL, Mahesh Vithalbhai; (57 pag.)WO2017/2089; (2017); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10534-59-5,Tetrabutylammonium acetate,as a common compound, the synthetic route is as follows.

Step 4: Preparation of tetrabutylammonium salt of (2S,5R)-N-[(3/?)-l-(ferf-butoxycarbonyl) piperidine-3-carbonyl]-6-(sulfooxy)-7-oxo-l,6-diazabicyclo[3.2.1]octane-2-carboxamide: To a stirred solution of (2S,5 ?)-N-[(3^)-l-(ieri-butoxycarbonyl)piperidine-3-carbonyl]-6-hydroxy-7-oxo- l,6-diazabicyclo[3.2.1]octane-2-carboxamide (0.480 g, 0.0012mol) in dimethylformamide (4.8 ml), at about 10C, was added dimethylformamide sulphur trioxide complex (0.207 g, 0.0013mol) in one portion. The reaction mass was stirred at the same temperature for 30 minutes and allowed to warm to room temperature. After 1 hour of stirring, to the reaction mixture was added, slowly, a solution of tetrabutylammonium acetate (0.408 g, 0.0013 mol) in dichloro methane (2 ml) and the stirring continued further. After 1 hour, the solvent from the reaction mixture was evaporated under reduced pressure to obtain an oily residue. The oily mass was co-evaporated with xylene (2×10 ml) resulting in a thick mass. This mass was partitioned between dichloromethane (10 ml) and water (10 ml) for three times. The combined organic extracts were washed with water (3×10 ml), dried (over anhydrous sodium sulphate) and the solvent was evaporated under reduced pressure. The resulting oily mass was triturated with ether (3×10 ml), each time the ether layer was decanted and finally the residue was concentrated under reduced pressure to obtain 0.7 g of the titled product as white foam in 80% yield.Analysis:475.4 (M-l) as free acid; for Molecular Weight: 717.95 and Molecular Formula:

10534-59-5, The synthetic route of 10534-59-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; KALE, Amol; SHAIKH, Mohammad Usman; PATEL, Mahesh Vithalbhai; (65 pag.)WO2016/116788; (2016); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

10534-59-5, Tetrabutylammonium acetate is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

A 2.0 mmol of CoBr2*H2O, 2.0 mmol of H2bpb (1) and 4.0 mmol triethylamine were dissolved in 20 ml of DMF and stirred at RT and air for 20 min. Then 4.42 mmol of NEt4Br was added and the solution was stirred at RT and air an additional 12 h. DMF was removed in vacuo and the residue was dissolved in 30 ml of acetonitrile and filtered. Through adding 30 ml of diethyl ether to the solution and cooling down to 2 C a brown precipitate was formed. After filtering, washing with diethyl ether and drying under vacuo the product was yielded as a brown powder (56%). The complex is air-stable in the solid state and can be stored for months without degradation.

10534-59-5, As the paragraph descriping shows that 10534-59-5 is playing an increasingly important role.

Reference£º
Article; Adolph; Zevaco; Walter; Dinjus; Doering; Polyhedron; vol. 48; 1; (2012); p. 92 – 98;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10534-59-5,Tetrabutylammonium acetate,as a common compound, the synthetic route is as follows.

General procedure: The solution of a receptor (~10-3 M) was titrated in NMR tube with the 0.1-0.3 M solution of arespective TBA salt. The solution of the salt contained a certain amount of the receptor to keep receptorconcentration constant during titration experiments. It was important to choose such volumes ofaliquots so that most of the data points could occur in close proximity of the inflection point of therespective titration curve; 11 to 23 data points were recorded. Such procedure allows for more precisecalculation of binding constants. A nonlinear curve fitting for the 1:1 binding model was carried outwith the HypNMR2008 Software [26-28] (Version 4.0.71) and allows the determination of the globalassociation constant. The details are given in ESI Figures S27-S65 and Tables S1-S38., 10534-59-5

The synthetic route of 10534-59-5 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Tyszka-Gumkowska, Agata; Pikus, Grzegorz; Jurczak, Janusz; Molecules; vol. 24; 14; (2019);,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.10534-59-5,Tetrabutylammonium acetate,as a common compound, the synthetic route is as follows.

To a stirred solution of (25,5 ?)-6- hydroxy-A^-(lH-imidazol- l-ylacetyl)-7-oxo- l,6-diazabicyclo[3.2.1]octane-2-carbohydrazide (10.3 g, 33.4 mmol, product obtained in step 4) in dimethylformamide (70 ml) was added dimethylformamide sulfur trioxide complex (6.45 g, 42.1 mmol). The reaction mixture was stirred at 10- 15C. The progress of reaction was monitored by thin layer chromatography using mixture of chloroform and methanol (8:2) as solvent. After completion of the reaction, solution of tetrabutyl ammonium acetate (12.69 g, 42 mmol) in water (43 ml) was added to the reaction mixture under stirring. After complete conversion to tetrabutylammoinum salt, the volatiles were removed under vacuum at 40-45 C. The obtained residue was partitioned in mixture of dichloro methane and water (140 ml + 140 ml). The organic layer was dried over anhydrous sodium sulfate and distilled to get 23 g of crude product. The crude product was purified by column chromatography using 100-200 mesh silica gel using mixture of chloroform and methanol as an eluent. The pure fractions were collected and were concentrated to obtain 12 g of tetrabutyl ammonium salt of (2S,5R)-iV-(lH- imidazol- l-ylacetyl)-7-oxo-6-(sulfooxy)- l,6-diazabicyclo[3.2.1]octane-2-carbohydrazide in 54.15% yield, 10534-59-5

As the paragraph descriping shows that 10534-59-5 is playing an increasingly important role.

Reference£º
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; DEKHANE, Deepak; SHAIKH, Mohammad Usman; BIRAJDAR, Satish; DOND, Bharat; PATEL, Mahesh Vithalbhai; (100 pag.)WO2017/81615; (2017); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

10534-59-5, Tetrabutylammonium acetate is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Step 3: Synthesis of tetrabutyl ammonium salt of (25)-pyrrolidin-2-yl-methyl {[(25, 5 f)-7- oxo-6-(sulfooxy)-l,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}carbamate: To a stirred solution of (25)-pyrrolidin-2-yl- methyl { [(25, 5R)-7-oxo-6-(hydroxy)-l,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl} carbamate (0.984 g, 0.002 mol) in dimethylformamide (10 ml) was added dimethylformamide sulfur trioxide complex (0.548 g, 0.0035 mol) in one portion under stirring at 10C. The reaction mass was stirred at the same temperature for 30 minutes and allowed to warm to room temperature. After 1 hour, a solution of tetrabutylammonium acetate (1.05 g, 0.0035 mol) in dicholoromethane (2 ml) was added to the reaction mixture under continuous stirring. After 1 hour of stirring the solvent from the reaction mixture was evaporated under reduced pressure to obtain an oily residue. The oily mass was co-evaporated with xylene (2×10 ml) to obtain thick mass. This mass was partitioned between dichloromethane (10 ml) and water (10 ml). The combined organic extracts were washed with water (3×10 ml) and dried over anhydrous sodium sulfate.The solvent was evaporated under reduced pressure and the resulting oily mass was triturated with ether (3×10 ml), each time the ether layer was decanted and finally the residue was concentrated under reduced pressure to obtain 1.2 g of the titled product as white foam in 80% yield., 10534-59-5

10534-59-5 Tetrabutylammonium acetate 82707, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; WOCKHARDT LIMITED; TADIPARTHI, Ravikumar; PATIL, Vijaykumar Jagdishwar; KALE, Amol; SHAIKH, Mohammad Usman; PATEL, Mahesh Vithalbhai; (65 pag.)WO2016/116788; (2016); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI

10534-59-5, Tetrabutylammonium acetate is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

To a solutionof 5 (1 mmol, 1 eq.), 1-bromo-3,5-dimethoxybenzene(1.5 eq.), TBAA (6.0 eq.), Pd(OAc)2 (0.1 eq.) were dissolvedin 2 cm3 of NMP under an argon atmosphere. The wholewas heated at 110 C for 24 h. After cooling, a saturatedsolution of Na2CO3 was added and the resulting solutionwas extracted thrice with ethyl acetate. The organic layerswere then dried over Na2SO4 and evaporated to give anoil, from which residual NMP was evacuated using a lyophilizer.Chromatography of the resulting oil on silica geleluted with hexane/ethyl acetate (v/v: 60/40) gave 7 (tracesin these conditions). Further elution gave 6 in 75% yield asan orange oil. MS (ESI): m/z = 412.10 ([M+H]+); 1H NMR(400 MHz CDCl3):= 1.77 (s, 3H), 2.80 (t, 2H, J = 6.9 Hz),3.55 (s, 6H), 3.58 (s, 3H), 4.14 (t, 2H, J = 6.9 Hz), 5.29(s, 2H), 6.21 (d, 2H, J = 2.3 Hz), 6.46 (t, 1H, J = 2.3 Hz),6.72 (d, 2H, J = 8.7 Hz), 6.93 (d, 2H, J = 8.7 Hz) ppm; 13CNMR (100 MHz, CDCl3):= 20.7, 24.8, 51.5; 55.1, 55.3,63.3, 101.3, 107.6, 113.9,127.6,128.6, 128.8, 135.1, 141.6,159.3, 160.9, 170.6 ppm.

10534-59-5, As the paragraph descriping shows that 10534-59-5 is playing an increasingly important role.

Reference£º
Article; Praud-Tabaries, Annie; Bottzeck, Olivier; Blache, Yves; Monatshefte fur Chemie; vol. 150; 4; (2019); p. 649 – 654;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI