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【结 构 式】

【分子编号】58115

【品名】(6R,7R)-7-{[4-bromo-2-(methoxyimino)-3-oxobutanoyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

【CA登记号】

【 分 子 式 】C14H16BrN3O7S

【 分 子 量 】450.26706

【元素组成】C 37.35% H 3.58% Br 17.75% N 9.33% O 24.87% S 7.12%

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:(III)

The condensation of 7-amino-3-(methoxymethyl)-3-cephem-4-carboxylic acid (I) with 4-bromo-2-(methoxyimino)-3-oxobutyric acid (II) by means of PCl5 and HMDS in dichloromethane gives the butyramide (III), which is cyclized with thiourea (IV) by means of Na-OAc in water to yield the thiazol derivative (IV). Finally, the carboxy group of (IV) is esterified with 1-iodoethyl isopropyl carbonate (VI) by means of DBU in DMA to afford the target cefpodoxime proxetil.

1 Kumar, Y.; Nizar, H.; Tewari, N.; Rai, B.P.; Aryan, R.C. (Ranbaxy Laboratories Ltd.); Process for the preparation of cefpodoxime acid. WO 0283634 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 43811 (6R,7R)-7-amino-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C9H12N2O4S 详情 详情
(II) 58114 4-bromo-2-(methoxyimino)-3-oxobutanoic acid;(Z)-4-bromo-2-(methoxyimino)-3-oxobutanoic acid C5H6BrNO4 详情 详情
(III) 58115 (6R,7R)-7-{[4-bromo-2-(methoxyimino)-3-oxobutanoyl]amino}-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C14H16BrN3O7S 详情 详情
(IV) 10180 Thiourea 62-56-6 CH4N2S 详情 详情
(V) 21558 (6R,7R)-7-[[2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino]-3-(methoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid C15H17N5O6S2 详情 详情
(VI) 58116 isopropyl 3-iodobutanoate C7H13IO2 详情 详情
Extended Information