Acetyl chloride → HCID 18367397, compound

Participants

Reaction Steps

To a solution of [3-[[2-(4,5-diphenyloxazol-2-yl)pyrrolidin-3-yl]methyl]phenoxy]acetic acid (140 mg) in a mixture of THF (10 ml) and water (10 ml) was added acetyl chloride (1.0 ml) dropwise at 0° C. keeping pH 8-9 with 1N NaOH solution. The mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, 1N-HCl and brine. The dried solvent was evaporated in vacuo and the residue was purified by trituration with hexane to afford [3-[[2-(4,5-diphenyloxazol-2-yl)-1-acetylpyrrolidin-3-yl]methyl]phenoxy]acetic acid (150 mg). FABMS (m/z): 497 (M+ +1) IR (Nujol): 3400, 1600 cm-1NMR (DMSO-d6, δ): 1.8-2.4 (5H, m), 2.6-3.1 (3H, m), 3.2-3.9 (2H, m), 4.58, 4.61 (2H, each s), 4.8-5.2 (1H, m), 6.6-7.0 (3H, m), 7.1-7.8 (11H, m)

Provenance & Evidence