Hydrochloric Acid → (2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid

Participants

Reaction Steps

To a round bottom flask was added (2R,5R)-methyl 2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoate (300 mg, 0.570 mmol), 2 M LiOH in water (5.0 mL, 10 mmol) and MeOH (5 mL). The reaction was stirred at rt for 2 days. The reaction mixture was then cooled in an ice-bath and aqueous 1 M HCl was added slowly to adjust the pH to 4. A white precipitant was formed. The product was collected by filtration and washed with water (2×5 mL) to give (2R,5R)-2,5-dibenzyl-6-oxo-6-((R)-2-oxo-1-phenylazepan-3-ylamino)hexanoic acid (280 mg, 0.546 mmol, 96% yield) as a white solid. Anal. Calcd. for C32H36N2O4 m/z 512.4. found: 513.3 (M+H)+.

Provenance & Evidence