Benzenepropanoic acid → HCID 88142219, compound

Participants

Reaction Conditions

Reaction Steps

The title A compound of Example 5 (622.2 mg, 1.5 mmol) was added to a solution of hydrocinnamic acid (225.3 mg, 1.5 mmol) in acetonitrile (7.5 mL) and cooled to 0° C. Hydroxybenzotriazole hydrate (229.5 mg, 1.5 mmol), N,N-diisopropylethylamine (287 μl, 1.65 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride were added sequentially. After 64 hours at 0° C., additional N,N-diisopropylethylamine (52 μl, 0.3 mmol) was added and the reaction was allowed to proceed for 24 hours at 25° C. The reaction mixture was then concentrated and stirred with pH 4.01 buffer solution for 10 minutes. The resulting precipitate was filtered, washed sequentially with pH 4.01 buffer (3×50 mL) and water (3×50 mL), and dried in vacuo yielding 476.9 mg of crude product. Purification by flash chromatography afforded 253.6 mg of product, which was crystallized from hexane/ethyl acetate yielding 230.6 mg of the title compound, m.p. 157° C., [α]D =-74.6° (c=0.50, CH3OH).

Provenance & Evidence