Enzymatic synthesis of (-)- and (+)-acetoxyhexamides and (-)- and (+)-hydroxyhexamides.
The enantioselective hydrolysis of (+/-)-4-(1-acetoxyethyl)-N-(cyclohexylcarbamoyl)-benzenesulfona mides 3 with lipase Amano P from Pseudomonas sp. in a water-saturated solvent gave (R)-4-(1-hydroxyethyl)-N-(cyclohexylcarbamoyl)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).
Akita
H
H
School of Pharmaceutical Sciences, Toho University, Chiba, Japan.
Kurashima
K
K
Nozawa
M
M
Kawana
T
T
Hirayama
K
K
Seri
K
K
Imamura
Y
Y
D000092:Acetohexamide / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D000107:Acetylation; D001549:Benzamides / Q000138:chemical synthesis* / Q000737:chemistry; D006868:Hydrolysis; D008049:Lipase / Q000737:chemistry*; D011549:Pseudomonas / Q000201:enzymology*; D012997:Solvents; D013237:Stereoisomerism; D014753:Vinyl Compounds; D000096926:Benzenesulfonamides
D000092:Acetohexamide; D001549:Benzamides; D008049:Lipase; D012997:Solvents; D014753:Vinyl Compounds; C020362:hydroxyhexamide; D000096926:Benzenesulfonamides; C011566:vinyl acetate