(6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[[(2S)-2-phenyl-2-sulfoethanoyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid -Drug Synthesis Database

【结构式】

【分子编号】32666

【品名】(6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[[(2S)-2-phenyl-2-sulfoethanoyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

【CA登记号】

【分子式】C₁₈H₁₈N₂O₉S₂

【分子量】470.481

【元素组成】C 45.95% H 3.86% N 5.95% O 30.61% S 13.63%

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 reaction of 7-aminocephalosporanic acid (I) with alpha-sulfophenylacetyl chloride (II) by means of NaOH and NaHCO3 in ether gives 7-(alpha-sulfophenylacetamido)cephalosporanic acid (III), which is then condensed with isonicotinamide (IV) by means of KSCN and pyridine in water.

参考文献中间体

合成目标

【1】 Nomura, H.; et al.; Semisynthetic beta-lactams antibiotics. VII. New semisynthetic cephalosporins derived from alpha-sulfophenylacetic acid. Heterocycles 1974, 2, 1, 67-72.
【2】 Morimoto, S.; et al.; Cephalosporin compounds. DE 2234280; ES 404745; FR 2146313; NL 7209811 .
【3】 Nomura, H.; et al.; Semisynthetic beta-lactam antibiotics. 6. Sulfocephalosporins and their antipseudomonal activities. J Med Chem 1974, 17, 12, 1312-15.
【4】 Blancafort, P.; Castaner, J.; Serradell, M.N.; Sweetman, A.J.; Cefsulodin. Drugs Fut 1980, 5, 2, 67.

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)	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)	32665	(1S)-2-chloro-2-oxo-1-phenyl-1-ethanesulfonic acid		C₈H₇ClO₄S	详情	详情
(III)	32666	(6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[[(2S)-2-phenyl-2-sulfoethanoyl]amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₈H₁₈N₂O₉S₂	详情	详情
(IV)	25191	isonicotinamide	1453-82-3	C₆H₆N₂O	详情	详情

Extended Information