Hydrochloric Acid → (S)-2-((S)-2-((S)-2-((tert-Butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylic acid

Participants

Reaction Steps

To a solution of (S)-methyl 2-((S)-2-((S)-2-((tert-butoxycarbonyl)(methyl)amino)propanamido)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate (1.34 g, 2.02 mmol) in THF (13.5 mL) and MeOH (6.7 mL) was added NaOH(aq.) (3N, 3.4 mL, 10.1 mmol). After 3 h, the reaction mixture was poured into a sep funnel containing EtOAc and 1N HCl. The aqueous layer was extracted with EtOAc (3×), and the combined organic extracts were dried over MgSO4, filtered and concentrated in vacuo to afford the title compound (1.25 g, 1.93 mmol, 95%) as a light yellow foam, which was used without further purification. MS (ESI+) m/z 649.3 (M+H)+.

Provenance & Evidence