【结 构 式】 |
【分子编号】48530 【品名】(1S)-1-(4-chlorophenyl)-1-ethanaminium (2S)-2-hydroxy-3,3-diphenylbutanoate 【CA登记号】 |
【 分 子 式 】C24H26ClNO3 【 分 子 量 】411.92808 【元素组成】C 69.98% H 6.36% Cl 8.61% N 3.4% O 11.65% |
合成路线1
该中间体在本合成路线中的序号:(XIII)A pilot plant process was further developed for the (S)-enantiomer. Darzens condensation of benzophenone (VIII) with methyl chloroacetate gave the glycidic ester (X). Epoxide opening in (X) with trimethylaluminum furnished methyl 2-hydroxy-3,3-diphenylbutyrate (XI), which was hydrolyzed to the corresponding acid (VI) by using KOH in isopropanol. Treatment of the racemic acid (VI) with (S)-1-(4-chlorophenyl)ethylamine (XII) provided the desired (S)-acid salt (XIII). This was finally condensed with 4,6-dimethyl-2-(methylsulfonyl)pyrimidine (XIV) in the presence of lithium amide to yield the title compound.
【1】 Jansen, R.; et al.; Structural similarity and its suprises: Endothelin receptor antagonists - Process research and development report. Org Process Res Dev 2001, 5, 1, 16. |
中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
---|---|---|---|---|---|---|
(VI) | 48526 | 2-hydroxy-3,3-diphenylbutyric acid | C16H16O3 | 详情 | 详情 | |
(VIII) | 18732 | benzophenone | 119-61-9 | C13H10O | 详情 | 详情 |
(IX) | 10257 | methyl 2-chloroacetate; methyl chloroacetate | 96-34-4 | C3H5ClO2 | 详情 | 详情 |
(X) | 21148 | methyl 3,3-diphenyl-2-oxiranecarboxylate | C16H14O3 | 详情 | 详情 | |
(XI) | 48528 | methyl 2-hydroxy-3,3-diphenylbutanoate | C17H18O3 | 详情 | 详情 | |
(XII) | 48529 | (S)-4-Chloro-alpha-methylbenzylamine; 1-(4-Chlorophenyl)ethylamine | 4187-56-8 | C8H10ClN | 详情 | 详情 |
(XIII) | 48530 | (1S)-1-(4-chlorophenyl)-1-ethanaminium (2S)-2-hydroxy-3,3-diphenylbutanoate | C24H26ClNO3 | 详情 | 详情 | |
(XIV) | 38714 | 4,6-dimethyl-2-(methylsulfonyl)pyrimidine; 4,6-dimethyl-2-pyrimidinyl methyl sulfone | C7H10N2O2S | 详情 | 详情 |