Water → HCID 69005164, compound

Temperature

-78 °C

Using 174 mg of 3-{3-[3-(2,4-dichlorophenoxy)-2(S)-hydroxypropoxy]phenyl}-2(S)-isopropoxypropanoic acid ethyl ester (Production example 279e) was dissolved in 5 ml of dichloromethane, and the mixture was cooled to −78° C. To the solution was added 0.15 ml (diethylamino) sulfur trifluoride, and stirring was continued at room temperature for 2 days. Water was added thereto, and the mixture was extracted with dichloromethane. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was removed. The residue was purified by silica gel column chromatography, to give 79 mg of 3-{3-[3-(2,4-dichlorophenoxy)-2 (R)-fluoropropoxy]phenyl}-2(S)-isopropoxypropanoic acid ethyl ester in the 7:1→5:1 hexane-ethyl acetate fraction. This product was dissolved in 4 ml of ethanol and 0.5 ml of tetrahydrofuran and 0.5 ml of 1N lithium hydroxide were added, and stirring was continued overnight at room temperature. The solution was acidified with 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, filtered and the solvent was removed. The residue was purified by silica gel column chromatography, to give 61 mg of the title compound in the 3:1→1:1 hexane-ethyl acetate fraction.

1. extractionthe mixture was extracted with dichloromethane
2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
3. filtrationfiltered
4. customthe solvent was removed
5. customThe residue was purified by silica gel column chromatography

ORD record

ord-5b12779459304545a3168e1b6192ce8a

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544835B2