3-Fluorobenzylic alcohol → HCID 69523283, compound

Participants

Reaction Steps

To a solution of [5-(4-fluorophenylcarbamoyl)pyrimidin-2-ylsulfanyl]acetic acid (40 mg, 0.13 mmol) in THF (1 mL) was added diisopropylethylamine (45 μL, 0.26 mmol) and TSTU (55 mg, 0.18 mmol). After stirring for 5 min, 3-fluorobenzyl alcohol (18 μL, 0.17 mmol) and DMAP (18 mg, 0.15 mmol) were added and the solution was stirred for 18 h. Ethyl acetate was added, and the reaction was quenched with 3% HCl. The layers were separated, and the organic layer was washed successively with 5% NaHCO3, water, and brine. The brown organic layer was passed through a plug of SiO2 and washed with 50% ethyl acetate/hexane. The filtrate was concentrated to afford a yellow solid. Flash chromatography through SiO2 using 25% ethyl acetate/hexane afforded 15.0 mg (28% yield) of the titled product as a white solid. ESI-MS m/z 416 (MH+), 414 (M−H)−.

Provenance & Evidence