Benzyl isocyanate → HCID 54483168, compound

Participants

Reaction Steps

To a solution of 4(S)-benzyl-3(S)-methylazetidin-2-one (50 mg, 0.28 mmol) in THF (4 mL) at −78°, lithium bis(trimethylsilyl)amide (280 μL, 280 mmol, 1 M in THF) was added. After 10 min, benzyl isocyanate (37.2 mg, 34.6 μL, 0.28 mmol) was added. Stirring was continued at −78° for 45 min. The reaction mixture was diluted with EtOAc (50 mL) and washed with aqueous NaHSO4 (1M) and brine, dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, 14% EtOAc in hexane) to give the title compound 4(S)-benzyl-3(S)-methyl-2-oxoazetidine-1-carboxylic acid benzylamide (23 mg, 27% yield) as a colorless oil. 1H-NMR (400 MHz, CDCl3) δ7.38-7.19 (m, 10H), 6.94 (t, J=5.1 Hz, 1H), 4.53 (dd, J=14.9, 6.0 Hz, 1 H), 4.48 (dd, J=14.9, 6.0 Hz, 1H), 3.90 (ddd, J=8.6, 3.2, 2.9 Hz, 1H), 3.53 (dd, J=13.7, 3.5 Hz, 1 H), 2.95 (qd, J=7.6, 2.5 Hz, 1H), 2.92 (dd, J=13.3, 8.9 Hz, 1H), 1.14 (d, J=7.6 Hz, 3H); FAB MS m/z 309.3 (MH+); HRMS calcd for C19H21N2O2: 309.1603 (MH+); found: 309.1614.

Provenance & Evidence