J-110441, -Drug Synthesis Database

【结构式】

【药物名称】J-110441

【化学名称】(1R,5S,6S)-2-(Benzothien-2-ylsulfanyl)-6-[1(R)-hydroxyethyl]-1-methylcarbapen-2-em-3-carboxylic acid sodium salt
　　　　　　(4R,5S,6S)-3-(1-benzothiophen-2-ylsulfanyl)-6-[1(R)-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid sodium salt

【CA登记号】165817-65-2

【分子式】C₁₈H₁₆NNaO₄S₂

【分子量】397.45032

【开发单位】Banyu (Originator)

【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, beta-Lactam Enhancers, beta-Lactamase Inhibitors, Carbapenems

合成路线1

Carbapenem-2-diphenylphosphate (I) was condensed with the sodium salt of 2-mercaptobenzothiophene (II) to give thioether (III). The p-nitrobenzyl group of (III) was then deprotected by hydrogenation over Pd/C in the presence of NaHCO3 to afford the corresponding carboxylic acid sodium salt.

参考文献中间体

【1】 Szumiloski, S.P.; Ratcliffe, R.W.; Waddell, S.T.; et al.; Benzothiazolylthio carbapenems: Potent anti-MRSA agents. Bioorg Med Chem Lett 1995, 5, 13, 1427.

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)	13224	4-nitrobenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate	90776-59-3	C₂₉H₂₇N₂O₁₀P	详情	详情
(II)	37709	sodium 1-benzothiophen-2-ylsulfide		C₈H₅NaS₂	详情	详情
(III)	37710	4-nitrobenzyl (4R,5S,6S)-3-(1-benzothiophen-2-ylsulfanyl)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₂₅H₂₂N₂O₆S₂	详情	详情

Extended Information

Drug NewChemical Entity Original Patent(1)