|
【结 构 式】 
|
【分子编号】31291 【品名】3-(4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl)-N-[(1S)-2-hydroxy-1-phenylethyl]-2-(2,2,2-trifluoroethoxy)propanamide 【CA登记号】 |
【 分 子 式 】C29H30F3N3O5 【 分 子 量 】557.5696296 【元素组成】C 62.47% H 5.42% F 10.22% N 7.54% O 14.35% |
合成路线1
该中间体在本合成路线中的序号：(VI)The chiral compound was prepared by several alternative procedures. Acid hydrolysis of the known racemic ester (I) gave carboxylic acid (II), which was converted into acid chloride (III) by using oxalyl chloride in benzene. This was either condensed with (S)-2-phenylglycinol (V) or with (S)-4-benzyloxazolidine-2-one (VI) to provide the diastereomeric mixtures of amides (VI) or imides (VII), respectively. After chromatographic separation of the required (S,S)-diastereoisomers, the title compound was obtained by acid hydrolysis of the (S,S)-amide or by hydrolysis of the corresponding imide with NaOH.
| 【1】 Haigh, D.; Rami, H.K. (SmithKline Beecham plc); Benzoxazoles and pyridine derivs. useful in the treatment of type II diabetes. EP 0772605; JP 1998503508; WO 9604260; WO 9604261 . |
| 【2】 Smith, S.A. (SmithKline Beecham plc); Use of an antagonist of PPAR-alpha and PPAR-gamma for the treatment of syndrom X. WO 9725042 . |
| 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) | 31288 | methyl 3-(4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl)-2-(2,2,2-trifluoroethoxy)propanoate | C22H23F3N2O5 | 详情 | 详情 | |
| (II) | 31289 | 3-(4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl)-2-(2,2,2-trifluoroethoxy)propionic acid | C21H21F3N2O5 | 详情 | 详情 | |
| (III) | 31290 | 3-(4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl)-2-(2,2,2-trifluoroethoxy)propanoyl chloride | C21H20ClF3N2O4 | 详情 | 详情 | |
| (IV) | 10973 | (2S)-2-Amino-2-phenyl-1-ethanol; (S)-2-Hydroxy-1-phenylethylamine; (S)-(+)-2-Phenylglycinol; (S)-2-Amino-2-phenyl-1-ethanol | 20989-17-7 | C8H11NO | 详情 | 详情 |
| (V) | 14694 | (S)-4-Benzyl-2-oxazolidinone; (4S)-4-Benzyl-1,3-oxazolan-2-one; (S)-(-)-4-Benzyl-2-oxazolidinone | 90719-32-7 | C10H11NO2 | 详情 | 详情 |
| (VI) | 31291 | 3-(4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl)-N-[(1S)-2-hydroxy-1-phenylethyl]-2-(2,2,2-trifluoroethoxy)propanamide | C29H30F3N3O5 | 详情 | 详情 | |
| (VII) | 31292 | (4S)-3-[3-(4-[2-[1,3-benzoxazol-2-yl(methyl)amino]ethoxy]phenyl)-2-(2,2,2-trifluoroethoxy)propanoyl]-4-benzyl-1,3-oxazolidin-2-one | C31H30F3N3O6 | 详情 | 详情 |