4-Methylmorpholine → HCID 86705898, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (R)-2-((tert-butoxycarbonyl)amino)-3-((2-methoxy-2-oxoethyl)thio)-3-methylbutanoic acid (0.19 g, 0.58 mmol) in DMF (4 mL) was added HATU (0.24 g, 0.62 mmol) at ice bath temperature. The reaction mixture was stirred at 0° C. for 10 min, followed by addition of a solution of benzyl ((S)-3,3-dimethyl-1-oxo-1-((2S,4R)-2-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-4-((S)-3-(((R)-1,2,3,4-tetrahydronaphthalen-1-yl)carbamoyl)-1,2,3,4-tetrahydroisoquinolin-7-yl)pyrrolidin-1-yl)butan-2-yl)carbamate (Compound A, 0.35 g, 0.44 mmol) in DMF (2 mL) and NMM (0.08 mL, 0.71 mmol). The resulting mixture was stirred at rt for 4 h. The reaction mixture was poured into a separatory funnel containing EtOAc and brine. The organic layer was separated and washed with sat. aq. NaHCO3 solution and brine successively. The organic layer was dried over MgSO4 and filtered. The filtrate was concentrated in vacuo. The residue was purified by flash chromatography (gradient elution from 0 to 60% EtOAc/DCM) to afford the title compound (0.40 g, 82%) as a white foam. MS (ESI+) m/z 1099.6 (M+H)+.

Provenance & Evidence