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【结 构 式】

【分子编号】16073

【品名】4-methoxybenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate

【CA登记号】

【 分 子 式 】C18H21NO6

【 分 子 量 】347.36788

【元素组成】C 62.24% H 6.09% N 4.03% O 27.64%

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:(I)

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.

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