benzyl (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】24157

【品名】benzyl (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【分子式】C₁₄H₁₄N₂O₃S

【分子量】290.34284

【元素组成】C 57.92% H 4.86% N 9.65% O 16.53% S 11.04%

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：(V)

The Wittig condensation of diphenylmethyl 2-[2-(benzyloxycarbonylamino)thiazol-4 yl-2-formyl acetate with benzyloxycarbonylmethylene triphenylphosphorane (II) in toluene or dioxane gives 2-[2-(benzyloxycarbonylamino)thiazol-4-yl]-4 (benzyloxycarbonyl)-2-butenoic acid diphenylmethyl ester (III), which is hydrolyzed partiaily wth trifluoroacetic acid and anisole to the 2-butenoic acid (IV). The condensation of (IV) with 7-beta-amino-3-cephem-4-carboxylic acid benzyl ester (V) by means of dicyclohexylcarbodiimide (DCC) in dichloromethane affords the protected final product (VI), which is finally debenzylated by means of AlCl3 and anisole in methylene chloride.

参考文献中间体

合成目标

【1】 Yoshida, T.; Synthesis and biological properties of 7Beta-[(Z)-2-(2-amino-4-thiazoyl)-4-carboxy-2-butenoylamino]-3-cephem-4-carboxilic acid (7432-S), a new oral cephem antibiotic. J Antibiot 1987, 40, 10, 1468.
【2】 Hamashima, Y. (Shionogi & Co. Ltd.); 7-Carboxyalkenoylamido-3-cephem-4-carboxylic acid derivs.. EP 0136721; ES 8604602; ES 8605278; ES 8700222; GB 2154580; GB 2198727; JP 1985078987; JP 1985163884; JP 1985246388; US 4634697; US 4748170 .
【3】 Castaner, J.; Prous, J.; 7432-S. Drugs Fut 1987, 12, 12, 1117.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	24153	benzhydryl 2-(2-[[(benzyloxy)carbonyl]amino]-1,3-thiazol-4-yl)-3-oxopropanoate	C₂₇H₂₂N₂O₅S	详情	详情
(II)	22668	benzyl 2-(triphenylphosphoranylidene)acetate	C₂₇H₂₃O₂P	详情	详情
(III)	22721	1-benzhydryl 5-benzyl (Z)-2-(2-[[(benzyloxy)carbonyl]amino]-1,3-thiazol-4-yl)-2-pentenedioate	C₃₆H₃₀N₂O₆S	详情	详情
(IV)	22689	(Z)-5-(benzyloxy)-2-(2-[[(benzyloxy)carbonyl]amino]-1,3-thiazol-4-yl)-5-oxo-2-pentenoic acid	C₂₃H₂₀N₂O₆S	详情	详情
(V)	24157	benzyl (6R,7R)-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₁₄H₁₄N₂O₃S	详情	详情
(VI)	24158	benzyl (6R,7R)-7-[[(Z)-5-(benzyloxy)-2-(2-[[(benzyloxy)carbonyl]amino]-1,3-thiazol-4-yl)-5-oxo-2-pentenoyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate	C₃₇H₃₂N₄O₈S₂	详情	详情

Extended Information