Hydrochloric Acid → HCID 178503694, compound

Participants

Reaction Steps

To a solution of [4-(L-histidyl)-2-phenylbenzoyl methionine methyl ester hydrochloride (98.9 mg, 0.200 mmol), prepared as in Example 184B, in THF/H2O (4:1, 20 mL) was added LiOH.H2O (68.5 mg, 1.60 mmol). The solution was stirred for 6 hours and then was treated with 1 M aqueous HCl (20 mL). The mixture was lyopholized to provide a white solid. Recrystallization from methanol afforded [4-(L-histidyl)-2-phenylbenzoyl]methionine hydrochloride (31 mg, 32%) as a white solid. 1H NMR (D2O) δ 1.68-1.82 (m, 1H), 1.88-1.99 (comp, 2H), 2.02 (s, 3H), 2.00-2.12 (m, 1H), 3.28-3.32 (m, 2H), 3.49 (d, 2H), 4.28-4.34 (m, 1H), 4.44 (t, 1H), 7.36-7.53 (comp, 8H), 7.57 (m, 1H), 8.67 (m, 1H); LRMS (CI): 482 (M+1)+, 701.

Provenance & Evidence