benzhydryl (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】37979

【品名】benzhydryl (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

【CA登记号】

【分子式】C₃₁H₂₆N₄O₄S₃

【分子量】614.77

【元素组成】C 60.57% H 4.26% N 9.11% O 10.41% S 15.65%

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：(IV)

The title compound has been prepared by two related procedures: Treatment of 3-hydroxy cephem derivative (I) with methanesulfonyl chloride and K2CO3 afforded mesylate (II), which was condensed with 2-mercapto-5-methyl-1,3,4-thiadiazole (III) in the presence of potassium tert-butoxide to give thioether (IV). The benzhydryl ester of (IV) was then deprotected by treatment with trifluoroacetic acid.

参考文献中间体

合成目标

【1】 Tawara, S.; Sasaki, H.; Matsumoto, S.; Takasugi, H.; Yoshida, Y.; Matsumoto, Y.; Matsuda, K.; Studies of anti-Helicobacter pylori agents. Part 2: New cephem derivatives. Bioorg Med Chem 2000, 8, 9, 2317.
【2】 Sasaki, H.; Takasugi, H.; Matsumoto, Y.; Yoshida, Y.; Matsuda, K.; Matsumoto, s.; Synthesis and anti-Helicobacter pylori activity of FR182024, a new cephem derivative. Bioorg Med Chem Lett 1999, 9, 21, 3123.
【3】 Yoshida, Y.; Sasaki, H.; Matsuda, K.; Takasugi, H. (Fujisawa Pharmaceutical Co., Ltd.); Cephem cpds. and pharmaceutical use thereof. EP 0796263; JP 1998510258; WO 9617850 .

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)	37977	benzhydryl (6R,7R)-3-hydroxy-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₂₈H₂₄N₂O₅S	详情	详情
(II)	25091	benzhydryl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₂₉H₂₆N₂O₇S₂	详情	详情
(III)	37978	5-methyl-1,3,4-thiadiazole-2-thiol; 5-methyl-1,3,4-thiadiazol-2-ylhydrosulfide	29490-19-5	C₃H₄N₂S₂	详情	详情
(IV)	37979	benzhydryl (6R,7R)-3-[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]-8-oxo-7-[(2-phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₃₁H₂₆N₄O₄S₃	详情	详情

Extended Information