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

H Akita, K Kurashima, M Nozawa, S Yamamura…

Index: Akita, Hiroyuki; Kurashima, Katsumi; Nozawa, Masako; Yamamura, Shigeo; Seri, Kenzi; Imamura, Yorishige Tetrahedron Asymmetry, 1998 , vol. 9, # 24 p. 4331 - 4340

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Citation Number: 10

Abstract

Enantioselective acetylation of (±)-4-(1-hydroxyethyl) benzenesulfonamide 6 withAcylase 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 ( ...