• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】49998

【品名】(3S)-3-amino-1-(3-chlorobenzyl)-2-pyrrolidinone

【CA登记号】

【 分 子 式 】C11H13ClN2O

【 分 子 量 】224.6898

【元素组成】C 58.8% H 5.83% Cl 15.78% N 12.47% O 7.12%

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:(XIII)

Coupling of N-Boc-L-methionine (VIII) with 3-chlorobenzylamine (IX) using PyBOP provided amide (X). Methylation of the sulfide group of (X) with iodomethane gave rise to the sulfonium salt (XI), which was further cyclized to pyrrolidinone (XII) by treatment with lithium bis(trimethylsilyl)amide in cold THF. Acid deprotection of the Boc group of (XII) furnished amine (XIII). This was finally subjected to reductive alkylation with aldehyde (VII) in the presence of sodium cyanoborohydride to provide the corresponding (imidazolylmethyl)amine.

1 Bell, I.M.; et al.; Design and biological activity of (S)-4-(5-{[1-(3-chlorobenzyl)-2-oxopyrrolidin-3-ylamino]methyl}imidazol-1-ylmethyl)benzonitrile, a 3-aminopyrrolidinone farnesyltransferase inhibitor with excellent cell potency. J Med Chem 2001, 44, 18, 2933.
2 Beshore, D.C.; Bell, I.M.; Gallicchio, S.N.; Sisko, J.T.; Zartman, C.B.; Lumma, W.C. Jr. (Merck & Co., Inc.); Inhibitors of prenyl-protein transferase. WO 0117992 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(VII) 38388 4-[(5-formyl-1H-imidazol-1-yl)methyl]benzonitrile C12H9N3O 详情 详情
(VIII) 34459 (3-chlorophenyl)methanamine; 3-chlorobenzylamine 4152-90-3 C7H8ClN 详情 详情
(IX) 17634 (2S)-2-[(tert-butoxycarbonyl)amino]-4-(methylsulfanyl)butyric acid; N-alpha-t-BOC-L-methionine 2488-15-5 C10H19NO4S 详情 详情
(X) 49995 tert-butyl (1S)-1-[[(3-chlorobenzyl)amino]carbonyl]-3-(methylsulfanyl)propylcarbamate C17H25ClN2O3S 详情 详情
(XI) 49996 [(3S)-3-[(tert-butoxycarbonyl)amino]-4-[(3-chlorobenzyl)amino]-4-oxobutyl](dimethyl)sulfonium iodide C18H28ClIN2O3S 详情 详情
(XII) 49997 tert-butyl (3S)-1-(3-chlorobenzyl)-2-oxopyrrolidinylcarbamate C16H21ClN2O3 详情 详情
(XIII) 49998 (3S)-3-amino-1-(3-chlorobenzyl)-2-pyrrolidinone C11H13ClN2O 详情 详情
Extended Information