Trifluoroacetic acid → HCID 67875849, compound

Participants

Reaction Steps

A solution of 1.75 g (0.0033 mole) of Boc-4-fluoro-3(R,S)-L-Valyl-N-Methyl-L-Leucyl-L-Alanine benzyl ester in 17 ml of dry methylene chloride was stirred and cooled at -10° C. as 17 ml of trifluoroacetic acid, which was previously cooled at the same temperature, was added. The reaction was stirred and kept at -5° C. for 16 hours, then poured carefully with stirring into a mixture of 21 g of sodium bicarbonate, ice, and 100 ml of methylene chloride. After 5 minutes the organic layer was separated and washed with 3×30 ml of saturated sodium bicarbonate solution. The methylene chloride layer was dried over magnesium sulfate, and evaporated in vacuo to give 1.38 g of a stiff oil as the product. The yield was 99% of theory and the FAB m.s. showed a molecular ion peak at 424.

Provenance & Evidence