tert-butyl N-(2-oxoethyl)carbamate → tert-Butyl 3-[N-((1R)-2-{4-[2-({2-[(tert-butoxy)carbonylamino]ethyl}-amino)phenyl]-piperidyl}-1-[(4-chlorophenyl)methyl]-2-oxoethyl)carbamoyl](3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate

Participants

Reaction Steps

The title compound was prepared according to the procedure described in Example 25 (Step a) using tert-butyl 3-(N-{(1R)-2-[4-(2-aminophenyl)piperidyl]-1-[(4-chlorophenyl)methyl]-2-oxoethyl}carbamoyl)(3S)-1,2,3,4-tetrahydroisoquinoline-2-carboxylate (Example 20) (462 mg, 0.75 mmol), tert-butyl N-(2-oxoethyl)carbamate (Aldrich) (131 mg, 0.83 mmol) and NaBH(OAc)3 (Aldrich) (176 mg, 0.83 mmol) in CH2Cl2 (20 mL). Purification by silica gel chromatography (1:10 McOH:EtOAc) provided the title compound as a white foam (386 mg). MS (ESI, pos. ion) m/z: 760 (M+1); (ESI, neg. ion) m/z: 758 (M−1). Calc'd for C42H54ClN5O6: 759.38.

Provenance & Evidence