反应详情

To a 50 mL round-bottomed flask equipped with stirring was added 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) followed by CH3CN (15 mL) and ethylisocyanate (Chemservice, Inc.) (45.6 mg. 0.80 mmol). The reaction mixture was stirred at RT for 16 h, then the solvent was removed in vacuo. The resulting yellow oil 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 (397 mg). MS (ESI, pos. ion) m/z: 674 (M+1); MS (ESI, neg. ion) m/z: 672 (M−1). Calc'd for C37H44ClN5O0: 673.30.

1. customTo a 50 mL round-bottomed flask equipped
2. stirringThe reaction mixture was stirred at RT for 16 h
3. customthe solvent was removed in vacuo
4. dissolutionThe resulting yellow oil was dissolved in EtOAc (20 mL)
5. washwashed with satd NaHCO3 (20 mL) and satd NaCl (20 mL)
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated in vacuo
9. customPurification by silica gel chromatography (100% EtOAc)