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

【结 构 式】

【分子编号】17641

【品名】ethyl 3-([[((3S)-1-[4-[amino(hydroxyimino)methyl]phenyl]-2-oxopyrrolidinyl)amino]carbonyl]amino)propanoate

【CA登记号】

【 分 子 式 】C17H23N5O5

【 分 子 量 】377.40032

【元素组成】C 54.1% H 6.14% N 18.56% O 21.2%

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:(IX)

The condensation of 4-aminobenzamide (I) with N-(tert-butoxycarbonyl)-L-methionine (II) by means of 2-chloro-1-methylpyridinium iodide (CMPI) and N-methylmorpholine (NMM) in DMF gives the corresponding methioninamide (III), which is cyclized by means of trimethylsulfonium iodide and K2CO3 in hot DMSO yielding the pyrrolidinone (IV). The dehydration of (IV) with trifluoroacetic anhydride in THF affords the corresponding nitrile (V), which is deprotected with dry HCl in ethyl acetate giving the amine (VI). The condensation of (VI) with beta-alanine ethyl ester (VII) and carbonyl diimidazole (CDI) in pyridine yields the substituted urea (VIII), which is treated with hydroxylamine hydrochloride and triethylamine in ethyl acetate to afford the N-hydroxybenzamidine (IX). Finally, this compound is hydrogenated with H2 over Pd/C in acetic acid.

1 Castañer, J.; Merlos, M.; Leeson, P.A.; Orbofiban Acetate. Drugs Fut 1998, 23, 11, 1190-1198.
2 Abood, N.A.; Flynn, D.L.; Laneman, S.A.; Nosal, R.; Schretzman, L.A. (Pharmacia Corp.); Process for the preparation of amidino phenyl pyrrolidine betal-alanine urea analogs. US 5484946 .
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) 16778 4-aminobenzamide; p-aminobenzamide 2835-68-9 C7H8N2O 详情 详情
(II) 17634 (2S)-2-[(tert-butoxycarbonyl)amino]-4-(methylsulfanyl)butyric acid; N-alpha-t-BOC-L-methionine 2488-15-5 C10H19NO4S 详情 详情
(III) 17635 tert-butyl (1S)-1-[[4-(aminocarbonyl)anilino]carbonyl]-3-(methylsulfanyl)propylcarbamate C17H25N3O4S 详情 详情
(IV) 17636 tert-butyl (3S)-1-[4-(aminocarbonyl)phenyl]-2-oxopyrrolidinylcarbamate C16H21N3O4 详情 详情
(V) 17637 tert-butyl (3S)-1-(4-cyanophenyl)-2-oxopyrrolidinylcarbamate C16H19N3O3 详情 详情
(VI) 17638 4-[(3S)-3-amino-2-oxopyrrolidinyl]benzonitrile C11H11N3O 详情 详情
(VII) 17639 beta-Alanine, ethyl ester; ethyl 3-aminopropanoate 924-73-2 C5H11NO2 详情 详情
(VIII) 17640 ethyl 3-[([[(3S)-1-(4-cyanophenyl)-2-oxopyrrolidinyl]amino]carbonyl)amino]propanoate C17H20N4O4 详情 详情
(IX) 17641 ethyl 3-([[((3S)-1-[4-[amino(hydroxyimino)methyl]phenyl]-2-oxopyrrolidinyl)amino]carbonyl]amino)propanoate C17H23N5O5 详情 详情
Extended Information