PRACTICAL SYNTHESIS OF T-3761, (S)-10-(1-AMINOCYCLOPROPYL)-9-FLUORO-3-METHYL-7-OXO-2,3-DIHYDRO-7H-PYRIDO[1,2,3-DE]-1,4-BENZOXAZINE-6-CARBOXYLIC ACID

被引：0

作者：

TODO, Y

TAKAGI, H

IINO, F

HAYASHI, K

TAKATA, M

KURODA, H

MOMONOI, K

NARITA, H

机构：

来源：

CHEMICAL & PHARMACEUTICAL BULLETIN | 1994年 / 42卷 / 12期

关键词：

FLUOROQUINOLONE; SYNTHESIS; AMINOCYCLOPROPYL SUBSTITUENT; PYRIDOBENZOXAZINE; ANTIBACTERIAL AGENT;

D O I：

暂无

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

An economical 11-step synthesis of T-3761 (1), a new quinolone antibacterial agent discovered by us, has been developed. Commercially available 2,3,4,5-tetrafluorobenzoic acid (2) has been transformed to 4-(1-acetaminocydopropyl)-2,3,5-trifluorobenzoic acid (10) in 6 steps (68% yield), including cyclopropane-ring formation of the 4-cyanomethylbenzoate intermediate (6) at its side chain. Conversion of 10 to the beta-keto ester 11 and a subsequent 2-step pyridoxazine annulation procedure afforded 13 (80% yield), which, on N,O-deprotection, provided 1 (48% overall yield from 2). The overall reaction sequence can be carried out without chromatographic purification of intermediates.

引用

页码：2629 / 2632

页数：4