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【结 构 式】

【分子编号】47196

【品名】4-nitrobenzyl (4S,5R)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[7-(methylsulfanyl)imidazo[5,1-b][1,3]thiazol-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate

【CA登记号】

【 分 子 式 】C23H22N4O6S2

【 分 子 量 】514.58304

【元素组成】C 53.68% H 4.31% N 10.89% O 18.66% S 12.46%

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:(VII)

Imidazothiazole (I) is converted into methylsulfanyl derivative (II) by first reaction with EtMgBr in THF followed by treatment with MeSSO2Me. Lithiation of derivative (II) by means of BuLi in THF/hexane, followed by reaction with tributyltin chloride and LiHMDS, provides tributyltin derivative (III), which is then condensed with carbapenem derivative (VI) by means of Pd(dba)3, P(2-furyl)3 and ZnCl2 in NMP to afford (VII). (Derivative (VI) in turn can be obtained by first cyclization of the diazo compound (IV) by means of ZnBr2 and Rh2Oct4 in MeOAc/THF to provide bicyclic ketoester (V), which is finally treated with triflic anhydride (Tf2O) and DIEA in acetonitrile. The target product is finally obtained by first N-alkylation of the imidazothiazole ring of (VII) with iodoacetamide (VIII) in acetonitrile followed by deprotection of the carboxylic acid by hydrogenation over Pd/C inTHF/H2O.

2 Lynch, J.E.; Liu, T.M.-H.; Volante, R.P. (Merck & Co., Inc.); Process for synthesizing carbapenem intermediates using a rhodium catalyst and Lewis acid. US 5493018 .
1 Sakakibara, S.; Takata, T.; Yamamoto, K.; Shitara, E.; Shibasaki, Y.; Shimizu, A.; Komiya, I.; CP5068, a new carbapenem: Synthesis and structure-activity relationships. 40th Intersci Conf Antimicrob Agents Chemother (Sept 17 2000, Toronto) 2000, Abst F-1236.
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) 47193 7-iodoimidazo[5,1-b][1,3]thiazole C5H3IN2S 详情 详情
(II) 47194 7-(methylsulfanyl)imidazo[5,1-b][1,3]thiazole; imidazo[5,1-b][1,3]thiazol-7-yl methyl sulfide C6H6N2S2 详情 详情
(III) 47195 7-(methylsulfanyl)-2-(tributylstannyl)imidazo[5,1-b][1,3]thiazole; methyl 2-(tributylstannyl)imidazo[5,1-b][1,3]thiazol-7-yl sulfide C18H32N2S2Sn 详情 详情
(IV) 38749 4-nitrobenzyl (4R)-2-diazo-4-[(2R,3S)-3-[(1R)-1-hydroxyethyl]-4-oxoazetidinyl]-3-oxopentanoate C17H18N4O7 详情 详情
(V) 22575 4-nitrobenzyl (2R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate C17H18N2O7 详情 详情
(VI) 38750 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[[(trifluoromethyl)sulfonyl]oxy]-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C18H17F3N2O9S 详情 详情
(VII) 47196 4-nitrobenzyl (4S,5R)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[7-(methylsulfanyl)imidazo[5,1-b][1,3]thiazol-2-yl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C23H22N4O6S2 详情 详情
(VIII) 47197 2-iodoacetamide 144-48-9 C2H4INO 详情 详情
Extended Information