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【结 构 式】

【分子编号】60185

【品名】ethyl methyliminoformate

【CA登记号】

【 分 子 式 】C4H9NO

【 分 子 量 】87.1216

【元素组成】C 55.15% H 10.41% N 16.08% O 18.36%

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:(B)

Dynamic kinetic resolution of 3-acetyl-1-benzyl-2-pyrrolidinone (I) by Ru-BINAP catalyzed hydrogenation provides the (hydroxyethyl) pyrrolidinone (II). Subsequent reduction of lactam (II) employing NaBH4-BF3•Et2O affords pyrrolidine (III). After debenzylation of (III) by hydrogenation over Pd/C, the resultant pyrrolidine (IV) is protected as the corresponding N-Alloc derivative (V) upon treatment with allyl chloroformate. Subsequent Swern oxidation of the alcohol function of (V) leads to the optically pure ketone (VI). Treatment of ketone (VI) with Me3SiOTf and Et3N, followed by condensation with the acetoxyazetidinone (VII) affords adduct (VIII). Acylation of azetidinone (VIII) with allyl oxalyl chloride (IX), followed by cyclization of the intermediate oxalimide in the presence of triethyl phosphite, gives rise to the carbapenem system ( X). Desilylation of (X) with tetrabutylammonium fluoride leads to alcohol (XI). Further palladium-catalyzed deprotection of both the Alloc and allyl ester groups of (XI) provides the pyrrolidinyl carbapenem (XII). Finally, introduction of the desired N-methyl formimidoyl group into (XII) is accomplished by treatment with ethyl N-methyl formimidate.

1 Hattori, K.; et al.; Synthesis and antibacterial evaluation of novel 2-[N-imidoylpyrrolidinyl] carbapenems. Bioorg Med Chem Lett 2002, 12, 3, 383.
2 Murata, M.; Chiba, T.; Tsutsumi, H.; Hattori, K.; Kuroda, S.; Ohtake, H.; Shirai, F. (Fujisawa Pharmaceutical Co., Ltd.); 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid cpds.. EP 0394991; JP 1990300187; US 5102877 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(A) 38115 3-[(chlorocarbonyl)oxy]-1-propene 2937-50-0 C4H5ClO2 详情 详情
(B) 60185 ethyl methyliminoformate C4H9NO 详情 详情
(I) 60175 3-acetyl-1-benzyl-2-pyrrolidinone C13H15NO2 详情 详情
(II) 60176 (3S)-1-benzyl-3-[(1R)-1-hydroxyethyl]-2-pyrrolidinone C13H17NO2 详情 详情
(III) 60177 (1R)-1-[(3R)-1-benzylpyrrolidinyl]-1-ethanol C13H19NO 详情 详情
(IV) 60178 (1R)-1-[(3R)pyrrolidinyl]-1-ethanol C6H13NO 详情 详情
(V) 60179 allyl (3R)-3-[(1R)-1-hydroxyethyl]-1-pyrrolidinecarboxylate C10H17NO3 详情 详情
(VI) 60180 allyl (3R)-3-acetyl-1-pyrrolidinecarboxylate C10H15NO3 详情 详情
(VII) 11687 (2R,3R)-3-((1R)-1-[[tert-butyl(dimethyl)silyl]oxy]ethyl)-4-oxoazetanyl acetate C13H25NO4Si 详情 详情
(VIII) 60181 allyl (3R)-3-{2-[(2R,3S)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxoazetidinyl]acetyl}-1-pyrrolidinecarboxylate C21H36N2O5Si 详情 详情
(IX) 15585 allyl 2-chloro-2-oxoacetate C5H5ClO3 详情 详情
(X) 60182 2-propenyl 6-(1-{[(1,1-dimethylethyl)(dimethyl)silyl]oxy}ethyl)-7-oxo-3-{1-[(2-propenyloxy)carbonyl]-3-pyrrolidinyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C26H40N2O6Si 详情 详情
(XI) 60183 2-propenyl 6-(1-hydroxyethyl)-7-oxo-3-{1-[(2-propenyloxy)carbonyl]-3-pyrrolidinyl}-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C20H26N2O6 详情 详情
(XII) 60184 6-(1-hydroxyethyl)-7-oxo-3-(3-pyrrolidinyl)-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid C13H18N2O4 详情 详情
Extended Information