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.
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页码：2629 / 2632
页数：4
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