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【结 构 式】

【分子编号】54037

【品名】tert-butyl (2S)-1-({(2-cyclopentylethyl)[2-(2-hydroxyethoxy)-2-oxoethyl]amino}carbonyl)-2-pyrrolidinecarboxylate

【CA登记号】

【 分 子 式 】C21H36N2O6

【 分 子 量 】412.52672

【元素组成】C 61.14% H 8.8% N 6.79% O 23.27%

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:(XI)

The condensation of ArgoGel-OH resin (I) with N-(Fmoc)-glycine (II) by means of DIC and DMAP gives the resin-bound Fmoc-glycine (III), which is deprotected with piperidine to yield the resin-bound glycine (IV). The reaction of (IV) with 2-nitrophenylsulfonyl chloride (V) affords the sulfonamide (VI), which is alkylated with 2-cyclopentylethanol (VII) by means of DIAD and PPh3 to provide the N-alkylated sulfonamide (VIII). The reaction of (VIII) with Ph-SH, DBU and pyridine gives the N-alkylated resin-bound glycine (IX), which is condensed with 1-(chlorocarbonyl)-L-proline tert-butyl ester (X) to yield the resin-bound dipeptide tert-butyl ester (XI). Hydrolysis of the ester group of (XI) with TFA affords the free resin-bound dipeptide (XII), which is condensed with 4,5-dimethylthiazole-2-amine (XIII) by means of PyBOP and DMAP to provide the corresponding prolinamide (XIV). Finally, this compound is treated with hydroxylamine in order to cleave the title compound from the resin by formation of the desired hydroxamic acid.

1 Lewis, J.G.; Wu, C.; Jacobs, J.; et al.; Iterative parallel synthesis-derived N-alkyl urea hydroxamic acids: A new class of peptide deformylase inhibitors. 41st Intersci Conf Antimicrob Agents Chemother (Dec 16 2001, Chicago) 2001, Abst F-358.
2 Patel, D.V.; Jacobs, J.W.; Lewis, J.; Ni, Z.-J. (Versicor, Inc.); Novel urea cpds., compsns. and methods of use and preparation. WO 0144178 .
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) 11295 Polyethylene glycol;1,2-Ethanediol;Monoethylene glycol; Ethylene glycol 107-21-1 C2H6O2 详情 详情
(II) 42131 2-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]acetic acid 29022-11-5 C17H15NO4 详情 详情
(III) 54030 2-hydroxyethyl 2-{[(9H-fluoren-9-ylmethoxy)carbonyl]amino}acetate C19H19NO5 详情 详情
(IV) 54031 2-hydroxyethyl 2-aminoacetate C4H9NO3 详情 详情
(V) 32624 2-Nitrobenzenesulfonyl chloride 1694-92-4 C6H4ClNO4S 详情 详情
(VI) 54032 2-hydroxyethyl 2-{[(2-nitrophenyl)sulfonyl]amino}acetate C10H12N2O7S 详情 详情
(VII) 54033 2-Cyclopentylethanol; 2-Hydroxyethylcyclopentane; alpha-Methylcyclopentanemethanol; Cyclopentylmethylcarbinol 766-00-7 C7H14O 详情 详情
(VIII) 54034 2-hydroxyethyl 2-{(2-cyclopentylethyl)[(2-nitrophenyl)sulfonyl]amino}acetate C17H24N2O7S 详情 详情
(IX) 54035 2-hydroxyethyl 2-[(2-cyclopentylethyl)amino]acetate C11H21NO3 详情 详情
(X) 54036 tert-butyl (2S)-1-(chlorocarbonyl)-2-pyrrolidinecarboxylate C10H16ClNO3 详情 详情
(XI) 54037 tert-butyl (2S)-1-({(2-cyclopentylethyl)[2-(2-hydroxyethoxy)-2-oxoethyl]amino}carbonyl)-2-pyrrolidinecarboxylate C21H36N2O6 详情 详情
(XII) 54038 (2S)-1-({(2-cyclopentylethyl)[2-(2-hydroxyethoxy)-2-oxoethyl]amino}carbonyl)-2-pyrrolidinecarboxylic acid C17H28N2O6 详情 详情
(XIII) 54039 4,5-dimethyl-1,3-thiazol-2-ylamine; 4,5-dimethyl-1,3-thiazol-2-amine C5H8N2S 详情 详情
(XIV) 54040 2-hydroxyethyl 2-{(2-cyclopentylethyl)[((2S)-2-{[(4,5-dimethyl-1,3-thiazol-2-yl)amino]carbonyl}pyrrolidinyl)carbonyl]amino}acetate C22H34N4O5S 详情 详情
Extended Information