Acetic Acid → HCID 57589818, compound

Participants

Reaction Steps

Ester 18 (127 mg, 0.20 mmol) was dissolved in 1 mL dry methanol at room temperature. 1 mL of a 0.5 M solution of ammonium fluoride in methanol (0.5 mmol, 2.5 equiv.) was added, then 60 mg acetic acid (1 mmol, 5 equiv). The reaction was stirred overnight under argon, diluted with 20 mL ethyl acetate and 20 mL saturated sodium bicarbonate solution. The water layer was washed with 3 portions of ethyl acetate, and the combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography eluting with 3:1 methylene chloride/ethyl acetate to yield 19 (72 mg, 69%). MS: 611.2 [M+H]+.

Provenance & Evidence