methyl (2S)-2-amino-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate -Drug Synthesis Database

【结构式】

【分子编号】19877

【品名】methyl (2S)-2-amino-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate

【CA登记号】

【分子式】C₂₂H₂₄N₂O₄

【分子量】380.44364

【元素组成】C 69.46% H 6.36% N 7.36% O 16.82%

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：(IV)

Oxazolylethanol (I) was coupled to N-Boc-L-tyrosine methyl ester (II) using Mitsunobu conditions in the presence of PPh3 and DEAD to give ether (III). Subsequent deprotection of the Boc group of (III) with trifluoroacetic acid afforded amine (IV), which was then condensed with methyl cyclohexanone-2-carboxylate (V) in boiling toluene to yield enamine (VI). Further heating of (VI) at 190 C in anisole in the presence of Pd/C resulted in aromatization of the cyclohexene ring to produce the anthranilate derivative (VII). Finally, selective hydrolysis of the aliphatic ester with LiOH under careful conditions provided the target monoester.

参考文献中间体

合成目标

【1】 Cobb, J.E.; Blanchard, S.G.; Boswell, E.G.; Brown, K.K.; Charifson, P.S.; Cooper, J.P.; Collins, J.L.; Dezube, M.; Henke, B.R.; Hull-Ryde, E.A.; Lake, D.H.; Lenhard, J.M.; Oliver, W. Jr; Oplinger, J.; Pentti, M.; Parks, D.J.; Plunket, K.D.; Tong, W.Q.; N-(2-Benzoylphenyl)-L-tyrosine PPARgamma agonists. 3. Structure-activity relationship and optimization of the N-aryl substituent. J Med Chem 1998, 41, 25, 5055.

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)	19874	2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)-1-ethanol		C₁₂H₁₃NO₂	详情	详情
(II)	19875	methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-(4-hydroxyphenyl)propanoate	4326-36-7	C₁₅H₂₁NO₅	详情	详情
(III)	19876	methyl (2S)-2-[(tert-butoxycarbonyl)amino]-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate		C₂₇H₃₂N₂O₆	详情	详情
(IV)	19877	methyl (2S)-2-amino-3-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]phenyl]propanoate		C₂₂H₂₄N₂O₄	详情	详情
(V)	19878	methyl 2-oxocyclohexanecarboxylate	41302-34-5	C₈H₁₂O₃	详情	详情
(VI)	19879	methyl 2-[((1S)-2-methoxy-1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]benzyl]-2-oxoethyl)amino]-1-cyclohexene-1-carboxylate		C₃₀H₃₄N₂O₆	详情	详情
(VII)	19880	methyl 2-[((1S)-2-methoxy-1-[4-[2-(5-methyl-2-phenyl-1,3-oxazol-4-yl)ethoxy]benzyl]-2-oxoethyl)amino]benzoate		C₃₀H₃₀N₂O₆	详情	详情

Extended Information