1,2-Dichloroethane → (S)-Methyl 2-((S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoyl)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate

Participants

Reaction Steps

To a 0° C. solution of (S)-2-((tert-butoxycarbonyl)amino)-3,3-dimethylbutanoic acid (473 mg, 2.04 mmol) and (S)-methyl 3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxylate (745 mg, 2.04 mmol) in CH2Cl2 (12.4 mL) was added EDC (471 mg, 2.45 mmol), HOAt (334 mg, 2.45 mmol) and NMM (675 μL, 6.14 mmol). The resulting reaction mixture was allowed to warm to room temperature overnight and then quenched with EtOAc and sat. NaHCO3. The aqueous layer was extracted with EtOAc (3×). The combined organic extracts were washed with 1N HCl (2×), sat. aq. NaCl solution (1×), dried over MgSO4, filtered and concentrated in vacuo to give the title compound (1.18 g, 2.045 mmol, 100%) as a light yellow foam, which was used without further purification. MS (ESI+) m/z 578.2 (M+H)+.

Provenance & Evidence