【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% |
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 |