Ammonia → [4-(3-Pyridylmethylamino)-2-phenylbenzoyl]methionineamide

Participants

Reaction Conditions

Reaction Steps

[4-(3-pyridylmethylamino)-2-phenylbenzoyl]methionine methyl ester (80 mg, 0.18 mmol), prepared as in Example 192C, was dissolved in methanol (5 mL), cooled to 0° C., and the solution was saturated with anhydrous ammonia. The reaction was sealed for 72 hours at ambient temperature. Evaporation to dryness afforded [4-(3-pyridylmethylamino)-2-phenylbenzoyl]methionineamide (78 mg). MS m/e 435 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.59 (m, 2H), 1.83 (m, 2H), 2.02 (s, 3H), 4.43 (s, 2H), 4.51 (m, 1H), 5.16 (s, 1H), 5.64 (m, 1H), 6.14 (m, 1H), 6.50 (d, J=3 Hz, 1H), 6.63 (m, 1H), 7.38 (m, 7H), 7.66 (m, 2H), 8.55 (m, 1H), 8.62 (m, 1H).

Provenance & Evidence