Category: 167316-27-0

167316-27-0, N-((1S,2S)-2-Amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide is a catalyst-ligand compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

[RUCL2 (RL6-P-CYMENE)] 2 (0.84g, 1. 37MMOL), ET3N (0.67g, 6. 66MMOL, 0.93mL), and (1S, 2S)-N-P-TOLUENESULFONYL-1, 2-DIPHENYLETHYLENEDIAMINE (L. OG, 2. 72MMOL, 1. 78MOL% based upon ketone) are combined in a 500ML 1N round bottom flask. Isopropanol (25 mL) and Et3N (0.67g, 6. 66MMOL, 0.93mL) is added, a reflux condenser is attached and the mixture is warmed under reflux, and maintained, for 1 hour. Cool to room temperature and concentrate in vacuo (rotovapor followed by vacuum pump) to furnish the catalyst as a brown powdery solid. To the catalyst is added anhydrous DMF (Aldrich Sure Seal, 225mL), followed in order by 2- chloroacetylpyridine (23. 88G, 0. 153MOL) and HCOOH/Et3N (5: 2, Fluka, 55ML). After ca. 2-3 minutes of stirring (room temperature) bubbles (presumed to be CO2) are apparent, emanating from the stirring vortex of the red-black solution. Reaction progress is monitored by reverse phase analytical HPLC, and after 75 minutes of stirring, the starting material had been consumed (95: 5 NAH2PO4/H3PO4 buffered water/CH3CN to 5: 95,17 minutes; retention time of starting chloroketone: 7.39 minutes, retention time of halohydrin 2.66 minutes). Quench the reaction by adding MEOH (25ML), stir 5 minutes and then the DMF, etc is removed in vacuo (cold finger rotovapor, vacuum pump) to give a red-black viscous oil. The crude material is taken up in ET2O/CH2CL2 (4: 1,1. 25L), placed in a 3L separatory funnel, wash with saturated aq. NAHC03 (1. OL), brine (1. OL), and dried (NA2S04). Filtration and concentration in vacuo affords the crude product as a red-orange oil which is purified by chromatography on a column of silica gel (70MM OD, 250g 230-400mesh, packed hexanes; compound applied in CH2CIZ/HEXANES 60: 40; eluted with HEXANES/ET20 (75: 25 2L; 65: 35 2L; 55: 45 2L; 350mL fractions) using the flash technique. Fractions 9-16 are combined to afford 14. 72G (61%) of the target halohydrin as pale yellow solid. Physical Characteristics: MP: 47-48C ; 1H-NMR (400MHZ, CDC13) : 8 = 8.65, 7.92, 7.58, 7.44, 5.13, 4.60, 3.91 ; IR (neat): 3138, 3074,3029, 3014,2974, 2964,2955, 2895,2862, 2848, 2472,2350, 2328,2305, 2261 CM-1 ; Anal. Found: C, 53.23 ; H, 5.12 ; N, 8. 82 ; Specific Rotation LA] D25 =-39 (c 0.94, CH2C12) ; Chiral HPLC Analysis (Chiracel OJ): 98: 2; 96% ee. [RUCL2 (N6-P-CYMENE)] 2 (0. 99G, 1. 61MMOL), Et3N (0.67g, 6. 66MMOL, 0. 93ML), and (1S, 2S)-N-P-TOLUENESULFONYL-1, 2-DIPHENYLETHYLENEDIAMINE (1. 18G, 3. 22MMOL, 2. 10MOL% based upon ketone) are combined in a 500ML 1N round bottom flask. i- PROH (25 mL) and Et3N (0.67g, 6. 66MMOL, 0. 93ML) are added, a reflux condenser is attached and the mixture is warmed under reflux, and maintained, for 1 hour. Cool to room temperature and concentrate in vacuo (rotovapor) to furnish the catalyst as an orange-brown powdery solid. To the catalyst is added anhydrous DMF (Aldrich Sure SEAL , 250mL), followed in order by 2-chloroacetylfuran (22.3g, 0. 154MOL) and HCOOH/Et3N (5: 2, Fluka, 55ML). After ca. 2-3 minutes of stirring (room temperature) bubbles (presumed to be C02) are apparent, emanating from the stirring vortex of the red-black solution. Reaction progress is monitored by reverse phase analytical HPLC, and after 65 minutes of stirring, the starting material had been consumed (95: 5 NAH2PO4/H3PO4 buffered water/CH3CN to 5: 95,17 minutes; retention time of starting chloroketone: 6.70 minutes, retention time of halohydrin 6.35 minutes). Quench the reaction by adding MEOH (25mL), stir 5 minutes and then the reaction mixture is poured into ice-water (1L) and the aqueous phase is saturated with salt. The mixture is transferred to a 2L separatory funnel with ether (500ML), shaken, and the organic phase is removed. The aqueous layer is extracted with ether (3X250mL) and the combined organic layers are wash with saturated aq. NAHC03 (0. 5L), brine (4X250ML), and dried (NA2S04). Filtration and concentration in vacuo affords the crude product as a red-orange oil (22.7g) that is triturated with ETHER/PENTANE (10: 90,4X 100ML). The combined triturates are concentrated in vacuo (take care as the halohydrin is volatile, hence the choice of ether/pentane as triturant and no removal of DMF in vacuo) to furnish the desired halohydrin R-1- (2-FURYL)-2- chloroethanol (16.03g, 71%) in good purity as determined by HPLC AND 1H-NMR. Physical Characteristics : 1H-NMR (400MHZ, CDC13) : 5 = 7.41, 6.32, 4.92, 3. 82, 2.58 ; IR (liq. ) 3373,2475, 2084,2023, 1940,1505, 1226,1151, 1142, 1089, 1068, 1012, 884, 818, 742 CM-1 ; MS (EI) M/Z (rel. intensity) 146 (13), 148 (4), 146 (13), 98 (4), 97 (base), 95 (4), 94 (2), 69 (6), 65 (2), 41 (7), 39 (3); HRMS (EI) found 146.0133 ; Specific Rotation [AD2S] =-18 (c 0.97, methanol); Chiral HPLC Analysis (Chiracel OJ) : 99: 1 ; 98% ee., 167316-27-0

The synthetic route of 167316-27-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Patent; PHARMACIA & UPJOHN COMPANY; WO2004/85414; (2004); 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.167316-27-0,N-((1S,2S)-2-Amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide,as a common compound, the synthetic route is as follows.

Under an atmosphere of argon, 134 mg (0.2 mmol) of [RuCl2(hexamethylbenzene)]2 147 mg (0.4 mmol) of (S,S)-TsDPEN, 183 mg (2.8 mmol ) of potassium hydroxide, 3 mL of methylene chloride, and 3 mL of water were placed in a 20 mL Schlenk tube and stirred at room temperature for 1 hour. The organic phase was washed with water several times, and sodium sulfate was then added to the organic phase to dry it. The organic phase was further dried with CaH2 and then filtered, the solvent was removed by distillation, and the residue was dried under vacuum. The violet crystals thus obtained were used directly in a reaction as a catalyst. By the same procedure as in Reference Example 1, Ru[(S,S)-Tsdpen] (1,2,3,4,5-pentamethylbenzene), Ru[(S,S)-Tsdpen] (1,2,4,5-tetramethylbenzene), Ru[(S,S)-Tsdpen] (1,3,5-trimethylbenzene), Ru[(S,S)-Tsdpen] (p-cymene), and Ru[(S,S)-Msdpen] (hexamethylbenzene) were synthesized. Furthermore, RuH[(R,R)-Tsdpen] (1,3,5-trimethylbenzene) was synthesized by carrying out the reaction of Reference Example 1 in 2-propanol.

167316-27-0, As the paragraph descriping shows that 167316-27-0 is playing an increasingly important role.

Reference£º
Patent; Kanto Kagaku Kabushiki Kaisha; EP1439159; (2004); 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.167316-27-0,N-((1S,2S)-2-Amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide,as a common compound, the synthetic route is as follows.

Step 2 Scheme:- S, ? //–/N/ TEAF, I—) N 0 N 0 0 Compound 2 Compound 3 S-TsDPENMaterials : – Material Wt (g) MW Moles Equivs Compound 2 9 402. 79 0. 0224 1 DMF 39.5 73.09 0.54 24.16 (Rh Cp*C12) 2 0.0691 618.0 1. 12 x 104 5. 0 x 10-3 S, S-Ts DPEN 0.0817 366.0 2. 23 x 104 10. 0 x 10-3 DMF 7.5 73.09 0.103 4.59 TEAF 4. 65–2. 50 Cp* = pentamethylcyclopentadiene A 250 ML jacketed reactor set up with overhead stirrer, condenser, thermocouple and sparge pipe situated below the level of the agitator was assembled. The purified Compound 2 (9g) was charged to the reactor with DMF (39.5g). Freshly made catalyst (Rh CP*CI2) 2 (69.1 mg) and ligand S, S-Ts DPEN (N-p-toluenesulphonyl-1, 2- diphenylethylene-1, 2-diamine, 817 mg) in DMF (7.5g) was then charged. The contents were cooled to 10C and a nitrogen sparge rate of 1.2 L/min was established. The agitation was on full at 400 RPM. A solution of TEAF (triethylamine : formic acid mixture in 2: 5 mole ratio, 4.65 mis) was added drop-wise over 11.5 hrs overnight. The reaction was quenched with water (50MIS), a 15C exotherm (10-25C) was observed upon addition of the first 20 mis. The remaining 30 mis was added at <20C (bath temperature: 0C). Toluene was then charged (60 mis) at 20C. The reaction mass was agitated and allowed to settle respectively for 30 minutes each. The sparge was switched off at this point. The bottom red aqueous phase was back extracted with toluene (3X50M1S). The three resulting toluene phases were combined with the first black/brown organic phase. The combined reaction mass was concentrated down to a residual mass of 14.18g. The material obtained was then subjected to 3 repeats of the reduction and work up procedure, using freshly prepared catalyst for each repeat, to achieve 87% conversion, and a product mass of 7.8 g., 167316-27-0

167316-27-0 N-((1S,2S)-2-Amino-1,2-diphenylethyl)-4-methylbenzenesulfonamide 6612782, acatalyst-ligand compound, is more and more widely used in various fields.

Reference£º
Patent; AVECIA LIMITED; WO2005/28437; (2005); A1;,
Metal catalyst and ligand design
Ligand Template Strategies for Catalyst Encapsulation – NCBI