反应详情

To a solution of (S)-3-(biphenyl-4-yl)-2-(tert-butoxycarbonylamino)propanoic acid (300 mg, 0.88 mmol) in DMF (1.5 mL) and DCM (1.5 mL) was added HATU (401 mg, 1.05 mmol) and triethylamine (0.37 mL, 2.64 mmol) followed by methylamine (0.46 mL, 0.91 mmol). The mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with sat NaHCO3 and extracted with EtOAc. The organic layer was washed with water (8 times), brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The obtained residue was purified by TLC preparation plates using 3% 2N Ammonia in MeOH in DCM to give (S)-tert-butyl 3-(biphenyl-4-yl)-1-(methylamino)-1-oxopropan-2-ylcarbamate (111 mg). HPLC retention time=1.66 minutes (condition B); MS (m+1)=355.1; 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.32 (s, 9H) 2.66 (d, J=4.8 Hz, 3H) 3.01 (d, J=6.3 Hz, 2H) 4.18-4.41 (m, 1H) 5.08 (br. s., 1H) 5.93 (d, J=4.3 Hz, 1H) 7.19 (d, J=8.1 Hz, 2H) 7.22-7.29 (m, 1H) 7.35 (t, J=7.6 Hz, 2H) 7.44 (d, J=8.1 Hz, 2H) 7.48 (d, J=7.3 Hz, 2H).

1. customThe reaction mixture was quenched with sat NaHCO3
2. extractionextracted with EtOAc
3. washThe organic layer was washed with water (8 times), brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated under reduced pressure
7. customThe obtained residue was purified by TLC preparation plates