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

【结 构 式】

【分子编号】47702

【品名】methyl 2-[(tert-butoxycarbonyl)amino]-3-[4-(5-pyrimidinyl)phenyl]propanoate

【CA登记号】

【 分 子 式 】C19H23N3O4

【 分 子 量 】357.40944

【元素组成】C 63.85% H 6.49% N 11.76% O 17.91%

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:(III)

The protected 4-pyrimidinylphenylalanine (III) was prepared by palladium-catalyzed coupling of the boronophenylalanine (I) with the 5-halopyrimidine (II). After acidic cleavage of the N-Boc protecting group of (III), the resultant amino ester (IV) was coupled with N-Boc-cycloleucine (V) to provide dipeptide (VI). Further acidic treatment of (VI) removed the N-Boc group to yield amine (VII). The chiral bromo acid (IX) was obtained by diazotization of D-valine (VIII) in the presence of HBr and KBr. Acylation of the racemic amine (VII) with bromo acid (IX) furnished the corresponding amide (X) as an epimeric mixture. The bromo group of (X) was finally displaced with potassium thioacetate to give the title thioacetate ester.

1 Gude, C.; Chan, K.; Firooznia, F.; et al.; Synthesis and biological activity of novel potent endothelin-converting enzyme-1 inhibitors. Bioorg Med Chem Lett 2001, 11, 3, 375.
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) 47701 methyl 2-[(tert-butoxycarbonyl)amino]-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]propanoate C21H32BNO6 详情 详情
(II) 38987 5-bromopyrimidine 4595-59-9 C4H3BrN2 详情 详情
(III) 47702 methyl 2-[(tert-butoxycarbonyl)amino]-3-[4-(5-pyrimidinyl)phenyl]propanoate C19H23N3O4 详情 详情
(IV) 47703 methyl 2-amino-3-[4-(5-pyrimidinyl)phenyl]propanoate C14H15N3O2 详情 详情
(V) 30890 1-[(tert-butoxycarbonyl)amino]cyclopentanecarboxylic acid C11H19NO4 详情 详情
(VI) 47704 methyl 2-[([1-[(tert-butoxycarbonyl)amino]cyclopentyl]carbonyl)amino]-3-[4-(5-pyrimidinyl)phenyl]propanoate C25H32N4O5 详情 详情
(VII) 47705 methyl 2-[[(1-aminocyclopentyl)carbonyl]amino]-3-[4-(5-pyrimidinyl)phenyl]propanoate C20H24N4O3 详情 详情
(VIII) 21056 (R)-(-)-Valine; D-Valine; (R)-alpha-Aminoisovaleric acid 640-68-6 C5H11NO2 详情 详情
(IX) 33158 (2R)-2-bromo-3-methylbutyric acid 565-74-2 C5H9BrO2 详情 详情
(X) 47706 methyl 2-[[(1-[[(2R)-2-bromo-3-methylbutanoyl]amino]cyclopentyl)carbonyl]amino]-3-[4-(5-pyrimidinyl)phenyl]propanoate C25H31BrN4O4 详情 详情
Extended Information