Boron tribromide → 3-cyclopentyl-2-(3-fluoro-4-hydroxy-phenyl)-N-thiazol-2-yl-propionamide

A solution of 3-cyclopentyl-2-(3-fluoro-4-methoxy-phenyl)-N-thiazol-2-yl-propionamide (prepared in Example 118, 305.4 mg, 0.87 mmol) in methylene chloride (8.7 mL) at 25° C. was treated with a 1.0M solution of boron tribromide in methylene chloride (8.75 mL, 8.75 mmol). This solution was stirred at 25° C. for 5 h. At this time, the reaction was cooled to 0° C. and quenched by the dropwise addition of a dilute aqueous ammonium hydroxide solution. The resulting solution was stirred at 0° C. for 15 min. This mixture was then poured into water (50 mL) and extracted with ethyl acetate (3×30 mL). The organics were dried over sodium sulfate, filtered, and concentrated in vacuo. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 50/50 hexanes/ethyl acetate) afforded 3-cyclopentyl-2-(3-fluoro-4-hydroxy-phenyl)-N-thiazol-2-yl-propionamide (212.7 mg, 72.5%) as a white solid: mp 199-201° C.: EI-HRMS m/e calcd for C17H19FN2O2S (M+) 334.1151 found 334.1152.

1. temperatureAt this time, the reaction was cooled to 0° C.
2. customquenched by the dropwise addition of a dilute aqueous ammonium hydroxide solution
3. stirringThe resulting solution was stirred at 0° C. for 15 min
4. additionThis mixture was then poured into water (50 mL)
5. extractionextracted with ethyl acetate (3×30 mL)
6. dry with materialThe organics were dried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated in vacuo

ORD-Eintrag

ord-17cd61d0da8640b6ad68b7bec30bf286

Quelldatensatz

uspto-grants-2001_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06320050B1