methyl 2-hydroxy-3,3-diphenylbutanoate -Drug Synthesis Database

【结构式】

【分子编号】48528

【品名】methyl 2-hydroxy-3,3-diphenylbutanoate

【CA登记号】

【分子式】C₁₇H₁₈O₃

【分子量】270.32812

【元素组成】C 75.53% H 6.71% O 17.76%

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)

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.

参考文献中间体

合成目标

【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

Extended Information