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