【结 构 式】 |
【分子编号】34513 【品名】methyl (2S)-2-(2-benzoylanilino)-3-(4-[2-[methyl(2-pyridinyl)amino]ethoxy]phenyl)propanoate 【CA登记号】 |
【 分 子 式 】C31H31N3O4 【 分 子 量 】509.60496 【元素组成】C 73.06% H 6.13% N 8.25% O 12.56% |
合成路线1
该中间体在本合成路线中的序号:(IX)The 2-aminobenzophenone derivative (III) was prepared by condensation of L-tyrosine methyl ester (I) with 2-benzoylcyclohexanone (II) in refluxing anisole, with concomitant dehydrogenation in the presence of Pd/C. Subsequent Mitsunobu coupling of (III) with 2-(N-Boc-N-methylamino)ethanol (V), prepared from aminoalcohol (IV) and Boc2O, afforded the Boc-protected aminoethyl ether (VI). After removal of the Boc group of (VI) by treatment with trifluoroacetic acid, condensation of the resulting secondary amine (VII) with 2-fluoropyridine (VIII) yielded the 2-aminopyridine derivative (IX). Finally, the methyl ester group of (IX) was hydrolyzed to the title carboxylic acid using LiOH.
【1】 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. |
【2】 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 |
---|---|---|---|---|---|---|
23767 | Methoxybenzene; Methyl phenyl ether; Anisole | 100-66-3 | C7H8O | 详情 | 详情 | |
(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) | 21434 | methyl (2S)-2-(2-benzoylanilino)-3-(4-hydroxyphenyl)propanoate | C23H21NO4 | 详情 | 详情 | |
(IV) | 13324 | 2-Methylaminoethanol; 2-(Methylamino)-1-ethanol | 109-83-1 | C3H9NO | 详情 | 详情 |
(V) | 34509 | tert-butyl 2-hydroxyethyl(methyl)carbamate | C8H17NO3 | 详情 | 详情 | |
(VI) | 34510 | methyl (2S)-2-(2-benzoylanilino)-3-(4-[2-[(tert-butoxycarbonyl)(methyl)amino]ethoxy]phenyl)propanoate | C31H36N2O6 | 详情 | 详情 | |
(VII) | 34511 | methyl (2S)-2-(2-benzoylanilino)-3-[4-[2-(methylamino)ethoxy]phenyl]propanoate | C26H28N2O4 | 详情 | 详情 | |
(VIII) | 34512 | 2-fluoropyridine | 372-48-5 | C5H4FN | 详情 | 详情 |
(IX) | 34513 | methyl (2S)-2-(2-benzoylanilino)-3-(4-[2-[methyl(2-pyridinyl)amino]ethoxy]phenyl)propanoate | C31H31N3O4 | 详情 | 详情 |