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【结 构 式】

【分子编号】41643

【品名】(4R)-1-methyl-4-sulfanyl-2-pyrrolidinone

【CA登记号】

【 分 子 式 】C5H9NOS

【 分 子 量 】131.1986

【元素组成】C 45.77% H 6.91% N 10.68% O 12.19% S 24.44%

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:(V)

Protection of alcohol (I) with TBDMSCl and imidazole gives silyl compound (II) which is N-methylated by means of NaH and MeI and then deprotected with HCl to yield derivative (III). Mesylation of (III) with MsCl in presence of Et3N followed by thioacetylation with AcSK (A) affords thioacetate (IV) which is then hydrolyzed with NaOMe to yield (V). Treatment of (VI) with diphenylphosphoryl chloride (B) and DIEA in acetonitrile yields (VII), which is then condensed with mercaptan (V) by means of DIEA in the same solvent to provide carbapenem (VIII). Deprotection of the carboxyl moiety of (VIII) by hydrogenation with H2 over Pd/C affords carboxylate (IX), which is finally esterified with pivaloyloxymethyl iodide (X) in N,N-dimethylacetamide or DMF.

1 Miyauchi, M.; Ohya, S.; Kawamoto, I.; Shibayama, T.; Kanno, O.; Synthesis and biological evaluation of new oral carbapenems with 1-methyl-5-oxopyrrolidin-3-ylthio moiety. J Antibiot 1999, 52, 10, 900.
2 Kawamoto, I.; Tanaka, T.; Endo, R.; Miyauchi, M.; Iwata, M. (Sankyo Co., Ltd.); 2-(Heterocyclylthio)carbapenem derivs. their preparation and their use as antibiotics. AU 8932386; EP 0337637; EP 0597821; JP 1990028180; JP 1990049783; US 5104867; US 5242914 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(B) 16074 Diphenyl phosphoryl chloride; 1,1'-Diphenylphosphoryl chloride; Chlorodiphenyl Phosphate; Diphenyl chlorophosphate; Diphenylchlorophosphate 2524-64-3 C12H10ClO3P 详情 详情
(A) 17190 potassium ethanethioate 10387-40-3 C2H3KOS 详情 详情
(I) 17188 (S)-4-hydroxy-2-pyrrolidone; (4S)-4-hydroxytetrahydro-2H-pyrrol-2-one; (S)-4-hydroxypyrrolidone 68108-18-9 C4H7NO2 详情 详情
(II) 41640 (4S)-4-[[tert-butyl(dimethyl)silyl]oxy]-2-pyrrolidinone C10H21NO2Si 详情 详情
(III) 41641 (4S)-4-hydroxy-1-methyl-2-pyrrolidinone C5H9NO2 详情 详情
(IV) 41642 S-[(3R)-1-methyl-5-oxopyrrolidinyl] ethanethioate C7H11NO2S 详情 详情
(V) 41643 (4R)-1-methyl-4-sulfanyl-2-pyrrolidinone C5H9NOS 详情 详情
(VI) 37720 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]heptane-2-carboxylate C17H18N2O7 详情 详情
(VII) 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
(VIII) 41644 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(3R)-1-methyl-5-oxopyrrolidinyl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C22H25N3O7S 详情 详情
(IX) 41645 sodium (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[[(3R)-1-methyl-5-oxopyrrolidinyl]sulfanyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate C15H19N2NaO5S 详情 详情
(X) 11159 iodomethyl pivalate C6H11IO2 详情 详情
Extended Information