反应详情

A solution of 1,1-dimethylethyl 4-{[3-({[(6-fluoro-3′-formyl-3-biphenylyl)methyl]amino}carbonyl)phenyl]methyl}-1-piperidinecarboxylate (74 mg, 0.14 mmol) in CH2Cl2 (5 mL) was mixed with 1,1-dimethylethyl (2S)-2-methyl-1-piperazinecarboxylate (26 mg, 0.14 mmol) and NaB(OAc)3H (45 mg, 0.21 mmol). The resulting mixture was stirred for 16 hours, diluted with dichloromethane (30 mL) and washed with brine (10 mL). The organic layer was collected, dried over Na2SO4 and concentrated under vacuum. The residue was purified by loading onto a 2 g amminopropyl SPE cartridge, eluting sequentially with DCM (3×5 mL), EtOAc (3×5 mL), and MeOH (3×5 mL). The DCM fractions were combined, and mixed with 2 mL of TFA. After stirring for 1 h, the mixture was concentrated under vacuum, and the residue thus obtained was purified by Gilson reverse phase HPLC, eluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min), to give the title compound (19 mg, 27%). LC/MS: m/z, 501 (M+H), 1.35 min.

1. washwashed with brine (10 mL)
2. customThe organic layer was collected
3. dry with materialdried over Na2SO4
4. concentrationconcentrated under vacuum
5. customThe residue was purified
6. washeluting sequentially with DCM (3×5 mL), EtOAc (3×5 mL), and MeOH (3×5 mL)
7. additionmixed with 2 mL of TFA
8. stirringAfter stirring for 1 h
9. concentrationthe mixture was concentrated under vacuum
10. customthe residue thus obtained
11. customwas purified by Gilson reverse phase HPLC
12. washeluting with acetonitrile/water/0.1% TFA (10/90 to 70/30, v/v, over 12 min)