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【结 构 式】

【分子编号】30892

【品名】tert-butyl (1R)-1-([[1-(aminocarbonyl)cyclopentyl]amino]carbonyl)-3-(methylsulfanyl)propylcarbamate

【CA登记号】

【 分 子 式 】C16H29N3O4S

【 分 子 量 】359.49008

【元素组成】C 53.46% H 8.13% N 11.69% O 17.8% S 8.92%

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:(IV)

This compound has been obtained by two related ways: 1) The reaction of 1-(tert-butoxycarbonylamino)cyclopentane-1-carboxylic acid (I) with ammonia, EDC and HOBT gives the amide (II), which is deprotected with 4N HCl and condensed with N-(tert-butoxycarbonyl)-D-methionine (III) by means of EDC and HOBT yielding the dipeptide (IV). The cyclization of (IV) with methyl iodide and NaH affords the pyrrolidinone (V), which is deprotected with HCl and condensed with 1-(benzyloxycarbonyl)-L-proline (VI) by means of EDC and HOBT giving the protected seudopeptide (VII). Finally, this compound is deprotected by hydrogenation with H2 over Pd/C. 2) The deprotection of (V) with HCl and its condensation with 1-(tert-butoxycarbonyl)-L-proline (VIII) by means of EDC and HOBT gives the protected seudopeptide (IX), which is finally deprotected with 4N HCl.

1 Evans, M.C.; et al.; Synthesis and dopamine receptor modulating activity of novel peptidomimetics of L-prolyl-L-leucyl-glycinamide featuring alpha,alpha-disubstituted amino acids. J Med Chem 1999, 42, 8, 1441.
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) 30890 1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid C11H19NO4 详情 详情
(II) 30891 tert-butyl 1-(aminocarbonyl)cyclopentylcarbamate C11H20N2O3 详情 详情
(III) 26710 (2R)-2-[(tert-butoxycarbonyl)amino]-4-(methylsulfanyl)butyric acid 5241-66-7 C10H19NO4S 详情 详情
(IV) 30892 tert-butyl (1R)-1-([[1-(aminocarbonyl)cyclopentyl]amino]carbonyl)-3-(methylsulfanyl)propylcarbamate C16H29N3O4S 详情 详情
(V) 30893 tert-butyl (3R)-1-[1-(aminocarbonyl)cyclopentyl]-2-oxopyrrolidinylcarbamate C15H25N3O4 详情 详情
(VI) 19113 (2S)-1-[(benzyloxy)carbonyl]-2-pyrrolidinecarboxylic acid 1148-11-4 C13H15NO4 详情 详情
(VII) 30894 benzyl (2S)-2-[([(3R)-1-[1-(aminocarbonyl)cyclopentyl]-2-oxopyrrolidinyl]amino)carbonyl]-1-pyrrolidinecarboxylate C23H30N4O5 详情 详情
(VIII) 16734 (2S)-1-(tert-butoxycarbonyl)tetrahydro-1H-pyrrole-2-carboxylic acid; N-alpha-t-BOC-L-proline; (2S)-1-(tert-butoxycarbonyl)-2-pyrrolidinecarboxylic acid C10H17NO4 详情 详情
(IX) 30895 tert-butyl (2S)-2-[([(3R)-1-[1-(aminocarbonyl)cyclopentyl]-2-oxopyrrolidinyl]amino)carbonyl]-1-pyrrolidinecarboxylate C20H32N4O5 详情 详情
Extended Information