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【结 构 式】

【分子编号】43145

【品名】tert-butyl (6R,7R)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C15H21NO6S

【 分 子 量 】343.40088

【元素组成】C 52.46% H 6.16% N 4.08% O 27.95% S 9.34%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(IIIa)

7-Aminocephalosporanic acid (I) was converted to tert-butyl ester (II) by treatment with isobutylene and sulfuric acid. Subsequent diazotization, followed by reaction with methanol and rhodium catalyst, provided the 7-methoxy derivative (IIIa-b) as a diastereomeric mixture. The desired 7S-isomer was then deprotected with trifluoroacetic acid in anisole, yielding carboxylic acid (IV). Coupling of acid (IV) with 3-iodobenzylamine (VI) via activation as the mixed anhydride (V) with ethyl chloroformate gave rise to amide (VII). The sulfide group of (VII) was finally converted into the title sulfone by oxidation with oxone.

1 Levy, M.A.; Gleason, J.G. (SmithKline Beecham plc); Interleukin converting enzyme and apoptosis. EP 0851760; JP 1999514345; WO 9707805 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(IIIa) 43145 tert-butyl (6R,7R)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C15H21NO6S 详情 详情
(IIIb) 43146 tert-butyl (6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C15H21NO6S 详情 详情
(I) 22747 (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C10H12N2O5S 详情 详情
(II) 32660 tert-butyl (6R,7R)-3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate C14H20N2O5S 详情 详情
(IV) 43147 (6R,7S)-3-[(acetoxy)methyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C11H13NO6S 详情 详情
(V) 43148   C14H17NO8S 详情 详情
(VI) 20865 3-iodobenzylamine; (3-iodophenyl)methanamine C7H8IN 详情 详情
(VII) 43149 ((6R,7S)-2-[[(3-iodobenzyl)amino]carbonyl]-7-methoxy-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-en-3-yl)methyl acetate C18H19IN2O5S 详情 详情
Extended Information