methyl (2S)-2-[(2-benzoyl-1-cyclohexen-1-yl)amino]-3-(4-hydroxyphenyl)propanoate -Drug Synthesis Database

【结构式】

【分子编号】21433

【品名】methyl (2S)-2-[(2-benzoyl-1-cyclohexen-1-yl)amino]-3-(4-hydroxyphenyl)propanoate

【CA登记号】

【分子式】C₂₃H₂₅NO₄

【分子量】379.45584

【元素组成】C 72.8% H 6.64% N 3.69% O 16.87%

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)

Condensation of L-tyrosine methyl ester (I) with 2-benzoylcyclohexanone (II) in the presence of Pd/C in boiling anisole produced the vinylogous amide intermediate (III) which, in the reaction conditions, experienced a dehydrogenation to furnish benzophenone (IV). Then, coupling of (IV) with 2-(5-methyl-2-phenyloxazol-4-yl)ethanol (V) under Mitsunobu conditions afforded ether (VI). Finally, the ester function of (VI) was hydrolyzed with LiOH to give the title acid.

参考文献中间体

合成目标

【1】 Martín, L.; Sorbera, L.A.; Leeson, P.A.; Castañer, J.; Farglitazar. Drugs Fut 2001, 26, 4, 354.
【2】 N-(2-Benzoylphenyl)-L-tyrosine PPARgamma agonists. 1. Discovery of a novel serieis of potent antihyperglycemic and antihyperlipidemic agents. J Med Chem 1998, 41, 25, 5020.
【3】 Willson, T.M.; Mook, R.A. Jr.; Kaldor, I.; Henke, B.R.; Deaton, D.N.; Collins, J.L.; Cobb, J.E.; Brackeen, M.; Sharp, M.J.; O'Callaghan, J.M.; Erickson, G.A.; Boswell, G.E. (Glaxo Wellcome plc); Substd. 4-hydroxy-phenylalkanoic acid derivs. with agonist activity to PPAR-gamma. EP 0888317; JP 2000507216; WO 9731907 .

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)	21431	methyl (2S)-2-amino-3-(4-hydroxyphenyl)propanoate	1080-06-4	C₁₀H₁₃NO₃	详情	详情
(II)	21432	2-benzoylcyclohexanone	3580-38-9	C₁₃H₁₄O₂	详情	详情
(III)	21433	methyl (2S)-2-[(2-benzoyl-1-cyclohexen-1-yl)amino]-3-(4-hydroxyphenyl)propanoate		C₂₃H₂₅NO₄	详情	详情
(IV)	21434	methyl (2S)-2-(2-benzoylanilino)-3-(4-hydroxyphenyl)propanoate		C₂₃H₂₁NO₄	详情	详情
(V)	19874	2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-1-ethanol		C₁₂H₁₃NO₂	详情	详情
(VI)	21436	methyl (2S)-2-(2-benzoylanilino)-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate		C₃₅H₃₂N₂O₅	详情	详情

Extended Information