Sodium Hydroxide → HCID 131720454, compound

Participants

Reaction Steps

Conversion to the Free Acid. Ac-Leu-Leu-Phe-OMe was dissolved in 150 mL of methanol and 26 mL of 1N sodium hydroxide was added and the rection was stirred 4 hours at which time the methanol was removed under reduced pressure and an additional 7 mL of sodium hydroxide was added. This water fraction was then washed with ethyl acetate (10 mL) and neutralized by the addition of 1N HCL. The resulting mixture was extracted with ethyl acetate 2×100 mL and the extract washed with 1N HCL, brine and dried over MgSO4, filtered and the solvents were removed under reduced pressure to give 7.56 g (94%) of Ac-Leu-Leu-Phe-OH as a white solid. The NMR (100 MHz, CDCl3) of the product acid bears striking resemblance to that of the precursor ester except for the loss of a signal at δ 3.6 and the appearance of a broad singlet at 10.1 (1H).

Provenance & Evidence