1,2-Dichloroethane → HCID 69152743, compound

Participants

Reaction Steps

To a 50 mL round-bottomed flask equipped with stirring was added a solution of tert-butyl 3-(N-((1R)-2-[4-(2-{[2-(1,3-dioxoisoindolin-2-yl)ethyl](methylsulfonyl)-amino}phenyl)piperidyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Step e) (433.5 mg, 0.5 mmol) in 3:1 EtOH:1,2-dichloroethane (15 mL) followed by hydrazine (Aldrich) (49 mg, 1.5 mmol). The reaction mixture was stirred at 60° C. for 12 h. The organic solvents were removed in vacuo to provide a white solid which was dissolved in EtOAc (20 mL) and washed with satd NaHCO3 (20 mL) and satd NaCl (20 mL). The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. Purification by silica gel chromatography (100% EtOAc) provided the title compound as a white foam (349 mg). MS (ESI, pos. ion) m/z: 738 (M+1); MS (ESI, neg. ion) m/z: 736 (M−1). Calc'd for C38H48ClN5O6S: 737.30.

Provenance & Evidence