2-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazole → Rac-2-ethoxy-3-{2-methyl-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-1h-indol-5-yl}-propionic acid ethyl ester

HRID 2181233Notes

Reaction equation

HRID 2181233 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:16])=[CH:10]2)[CH3:2].Cl[CH2:22][C:23]1[N:24]=[C:25]([C:29]2[CH:34]=[CH:33][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:31][CH:30]=2)[O:26][C:27]=1[CH3:28]>>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[N:12]([CH2:22][C:23]1[N:24]=[C:25]([C:29]3[CH:30]=[CH:31][C:32]([C:35]([F:38])([F:37])[F:36])=[CH:33][CH:34]=3)[O:26][C:27]=1[CH3:28])[C:11]([CH3:16])=[CH:10]2)[CH3:2]

Participants

3

Reactant 2

HCID 102363332-(4-Trifluoromethylphenyl)-4-chloromethyl-5-methyloxazoleHCID 69563210HCID 69563210, compound

Product 1

HCID 69564405Rac-2-ethoxy-3-{2-methyl-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-1h-indol-5-yl}-propionic acid ethyl ester

Procedure

In analogy to the procedures described in examples 36a) and 36b), rac-2-ethoxy-3-(2-methyl-1H-indol-5-yl)-propionic acid ethyl ester (preparation 5) was reacted with 4-chloromethyl-5-methyl-2-(4-trifluoromethyl-phenyl)-oxazole to give rac-2-ethoxy-3-{2-methyl-1-[5-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-4-ylmethyl]-1H-indol-5-yl}-propionic acid ethyl ester, which was subsequently saponified to yield the title compound as colorless oil.

Sources & evidence

ORD record
ord-d906905656cf431ca8b36f41211bda1f
Source dataset
uspto-grants-2005_05
Patent number
US06890947B2

Reaction notes

Loading…