Sodium Hydroxide → N-{2(S)-[(4-Nitrobenzylthio)acetamido]-3(S)-methylpentyl}-N-(1-naphthylmethyl)-glycyl-methionine

Participants

Reaction Conditions

Reaction Steps

N-{2(S)-[(4-Nitrobenzylthio)acetamido]-3(S)-methylpentyl}-N-(1-naphthylmethyl)-glycyl-methionine methyl ester (from Example 1; 100 mg, 150 μmol) was dissolved in MeOH (1 mL) and 1.0N NaOH (300 μL, 300 μmol) was added. The mixture was stirred at 45° C. under argon for 45 minutes then the solution was partitioned between EtOAc (100 mL) and 5% citric acid (50 mL). The organic layer was washed with H2O (2×50 mL), dried (MgSO4), filtered and evaporated to give the title compound. 1H NMR; δ0.84 (t, 3H, J=7.5 Hz), 0.88 (d, 3H, J=7 Hz), 0.91-1.0 (m, 1H), 1.0-1.2 (m, 1H), 1.2-2.1 (m, 5H), 1.90 (s, 3H), 2.8-2.86 (m, 2H), 3.0-3.3 (m, 4H), 3.90 (s, 2H), 3.91-4.22 (m, 4H), 7.37-7.56 (m, 6H), 7.78-7.88 (m, 2H), 8.15 (d, 2H, J=8 Hz), 8.27 (d, 1H, J=8.3 Hz).

Provenance & Evidence