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【结 构 式】

【分子编号】62798

【品名】1-benzyl 2-methyl (2R)-1,2-pyrrolidinedicarboxylate

【CA登记号】

【 分 子 式 】C14H17NO4

【 分 子 量 】263.29332

【元素组成】C 63.87% H 6.51% N 5.32% O 24.31%

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:(II)

Esterification of N-benzyloxycarbonyl-D-proline (I) with MeOH in the presence of EDC, followed by deprotection of the resultant N-Cbz amino ester (II) with H2 and Pd(OH)2 leads to D-proline methyl ester (III). Subsequent coupling of (III) with N-benzyloxycarbonyl-O-t-butyl-L-4-trans-hydroxyproline (IV) yields the protected dipeptide (V). After removal of the N-benzyloxycarbonyl group of (V) by catalytic hydrogenolysis, the free amine (VI) is acylated by 3,3,3-triphenylpropionic acid (VII), producing amide (VIII). The methyl ester group of (VIII) is then hydrolyzed under alkaline conditions to furnish acid (IX).

1 Sagara, Y.; Kimura, T.; Fujikawa, T.; Noguchi, K.; Ohtake, N.; Identification of novel muscarinic M3 selective antagonists with a conformationally restricted Hyp-Pro spacer. Bioorg Med Chem Lett 2003, 13, 1, 57.
2 Kimura, T.; Noguchi, K.; Otake, N.; Uchiyama, M.; Naya, A.; Sagara, Y.; Numazawa, T.; Fujikawa, T. (Banyu Pharmaceutical Co., Ltd.); Novel amide derivs.. EP 1213281; WO 0107406 .
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) 17005 (2R)-1-[(benzyloxy)carbonyl]tetrahydro-1H-pyrrole-2-carboxylic acid C13H15NO4 详情 详情
(II) 62798 1-benzyl 2-methyl (2R)-1,2-pyrrolidinedicarboxylate C14H17NO4 详情 详情
(III) 36811 methyl (2R)-2-pyrrolidinecarboxylate C6H11NO2 详情 详情
(IV) 62799 (2S,4R)-1-[(benzyloxy)carbonyl]-4-(tert-butoxy)-2-pyrrolidinecarboxylic acid C17H23NO5 详情 详情
(V) 62800 benzyl (2S,4R)-4-(tert-butoxy)-2-{[(2R)-2-(methoxycarbonyl)pyrrolidinyl]carbonyl}-1-pyrrolidinecarboxylate C23H32N2O6 详情 详情
(VI) 62801 methyl (2R)-1-{[(2S,4R)-4-(tert-butoxy)pyrrolidinyl]carbonyl}-2-pyrrolidinecarboxylate C15H26N2O4 详情 详情
(VII) 57640 3,3,3-Triphenylpropionic acid; Tritylacetic acid 900-91-4 C21H18O2 详情 详情
(VIII) 62802 methyl (2R)-1-{[(2S,4R)-4-(tert-butoxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidinyl]carbonyl}-2-pyrrolidinecarboxylate C36H42N2O5 详情 详情
(IX) 62803 (2R)-1-{[(2S,4R)-4-(tert-butoxy)-1-(3,3,3-triphenylpropanoyl)pyrrolidinyl]carbonyl}-2-pyrrolidinecarboxylic acid C35H40N2O5 详情 详情
Extended Information