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【结 构 式】 
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【分子编号】19878 【品名】methyl 2-oxocyclohexanecarboxylate 【CA登记号】41302-34-5 |
【 分 子 式 】C8H12O3 【 分 子 量 】156.18148 【元素组成】C 61.52% H 7.74% O 30.73% |
合成路线1
该中间体在本合成路线中的序号：(V)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.
| 【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 |