Diethyl Ether → {3-Ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid

A 1 M aqueous solution of LiOH (2.3 ml, 2.3 mmol) was added to a solution of {3-ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester (577 mg, 1.15 mmol) in THF (6 ml). After stirring for 1 h at ambient temperature, additional 0.58 ml of the 1N LiOH solution were added and the reaction mixture was stirred for further 2.5 h. Diethyl ether (10 ml) was added, the resulting precipitate was filtered off and redissolved in ethyl acetate and 25% aqueous HCl solution (2 ml). The organic layer was washed with water and dried over sodium sulfate. Removal of the solvent under reduced pressure gave 365 mg (0.77 mmol, 67%) {3-ethyl-5-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-indol-1-yl}-acetic acid.

1. stirringthe reaction mixture was stirred for further 2.5 h
2. filtrationthe resulting precipitate was filtered off
3. dissolutionredissolved in ethyl acetate
4. washThe organic layer was washed with water
5. dry with materialdried over sodium sulfate
6. customRemoval of the solvent under reduced pressure

ORD record

ord-901015731c3b4e7cbb72652a8d89e20d

Source dataset

uspto-grants-2007_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07235572B2