tert-butyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-sulfanyltetrahydro-1H-pyrrole-1-carboxylate -Drug Synthesis Database

【结构式】

【分子编号】16076

【品名】tert-butyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-sulfanyltetrahydro-1H-pyrrole-1-carboxylate

【CA登记号】

【分子式】C₁₀H₂₁N₃O₄S₂

【分子量】311.42656

【元素组成】C 38.57% H 6.8% N 13.49% O 20.55% S 20.59%

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 reaction of (1R,6S)-6-[1(R)-hydroxyethyl]-1-methyl-2-oxo-1-carbapenam-3-carboxylic acid 4-methoxybenzyl ester (I) with diphenyl chlorophosphate (II) and ethyl diisopropylamine in acetonitrile gives the corresponding penem diphenylphosphate (III), which is condensed with 1-(tert-butoxycarbonyl)-2(S)-sulfamoylaminomethyl)pyrrolidine-4(S)-thio l (IV) by means of ethyl diisopropylamine in the same solvent, yielding compound (V), which is finally treated with AlCl3 to eliminate the protecting groups to obtain S-4661.

参考文献中间体

合成目标

【1】 Sendo, Y.; Kii, M.; Nishitani, Y.; Irie, T.; Nishino, Y. (Shionogi & Co., Ltd.); A production method for sulfamide. EP 0557122 .
【2】 Castaner, J.; Mealy, N.; Rabasseda, X.; S-4661. Drugs Fut 1995, 20, 4, 367.
【3】 Nishitani, Y.; Irie, T.; Nishino, Y. (Shionogi & Co. Ltd.); A pyrrolidylthiocarbapenem derivative. EP 0528678; JP 1993294970; US 5317016 .

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)	16073	4-methoxybenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate		C₁₈H₂₁NO₆	详情	详情
(II)	16074	Diphenyl phosphoryl chloride; 1,1'-Diphenylphosphoryl chloride; Chlorodiphenyl Phosphate; Diphenyl chlorophosphate; Diphenylchlorophosphate	2524-64-3	C₁₂H₁₀ClO₃P	详情	详情
(III)	16075	4-methoxybenzyl (4R,5R,6S)-3-[(diphenoxyphosphoryl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₃₀H₃₀NO₉P	详情	详情
(IV)	16076	tert-butyl (2S,4S)-2-[[(aminosulfonyl)amino]methyl]-4-sulfanyltetrahydro-1H-pyrrole-1-carboxylate		C₁₀H₂₁N₃O₄S₂	详情	详情
(V)	16077	4-methoxybenzyl (4R,5S,6S)-3-[[(3S,5S)-5-[[(aminosulfonyl)amino]methyl]-1-(tert-butoxycarbonyl)pyrrolidinyl]sulfanyl]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate		C₂₈H₄₀N₄O₉S₂	详情	详情

Extended Information