220948-23-2

Upstream product

• 220948-20-9 (S)-(-)-4-(1-hydroxyethyl)benzenesulfonamide 
• 113412-15-0 (+/-)-4-(1-hydroxyethyl)benzenesulfonamide 
• 138-38-5 4-ethylbenzenesulfonamide 
• 1565-17-9 4-acetylbenzenesulfonamide 
• 16712-69-9 p-ethylbenzenesulfonyl chloride 
• 220948-18-5 (+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)benzenesulfonamide 
• 3173-53-3 Cyclohexyl isocyanate 
• 220948-22-1 Acetic acid (S)-1-(4-sulfamoyl-phenyl)-ethyl ester 

Relevant academic research and scientific papers

Enzymatic synthesis of (-)- and (+)-acetoxyhexamides and (-)- and (+)hydroxyhexamides

The enantioselective hydrolysis of (±)-4-(1-acetoxyethyl)-N- (cyclohexylcarbamoyl)-benzenesulfonamides 3 with lipase Amano P from Pseudomonas sp. in a water-saturated solvent gave (R)-4-(1-hydroxyethyl)-N- (cyclohexylearbamoyl)benzenesulfonamide 2 (39%, >99% ee) and unchanged (S)-3 (50%, 62% ee). On the other hand, enantioselective esterification of (±)-2 with lipase Amano P in the presence of vinyl acetate provided (R)-3 (41%, >99% ee) and unchanged (S)-2 (46%, 78% ee).

Determination of absolute configuration of a metabolite (-)- hydroxyhexamide from acetohexamide, syntheses of (-)- and (+)- hydroxyhexamides and (-)- and (+)-acetoxyhexamides

Enantioselective acetylation of (±)-4-(1- hydroxyethyl)benzenesulfonamide 6 with 'Acylase I' (No. A 2156) from Aspergillus melleus in the presence of vinyl acetate gave (R)-4-(1- acetoxyethyl)benzenesulfonamide 7 (98% ee) and (S)-6 (98% ee). Both (S)-6 and (R)-7 were individually converted to the (S)-hydroxyhexamide 2 (>99% ee) and (R)-hydroxyhexamide 2 (>99% ee), respectively. The absolute configuration of a metabolite (-)-hydroxyhexamide 2 from acetohexamide 1 was found to be S based on unequivocal chemical methods including X-ray analysis.