Nitrogen → HCID 69904058, compound

Participants

Reaction Steps

To a stirred and ice-cooled slurry of (3S*,4R*)-1-tert-Butyldimethylsilyl-3-(2-hydroxymethyl-2-propenyl)-4-phenyl-2-azetidinone (13.66 g, 41.0 mmol), 2,6-lutidine (15.3 ml, d0.920, 123 mmol), and LiCl (anhydros, 4.37 g, 103 mmol) in DMF (103 ml) was added MeSO2Cl (MsCl, 7.93 ml, d1.480, 103 mmol) dropwise under an atmosphere of N2. After the reaction mixture was stirred with ice-cooling for 5 hours and 50 minutes, H2O (40 ml) was added. The stirring was continued at room temperature for additional 20 minutes to destroy the excess MsCl. The resultant dark red mixture was poured into H2O (70 ml). The mixture was extracted with Et2O (70 ml×5). The combined Et2O extracts were washed with H2O (×3), sat. NaHCO3 aq. solution (×1), and sat. NaCl aq. solution (×1), dried (MgSO4), treated with activated charcoal, and concentrated in vacuo to give practically pure title compound (15.36 g, quantitative) as a pale yellow oil. IRmax (film): 1735(v.s), 1650(w), 1175(s), 825(s), 750(s), 700(s) cm-1 ; 1H-NMR δ: 7.43-7.25(m, 5H), 5.14(br.s, 1H), 4.87(br.s, 1H), 4.22(d, J=2.6 Hz, 1H), 3.99(s, 2H), 3.25(ddd, J=10.1, 5.1, 2.6 Hz, 1H), 2.78(dd, J=16.1, 5.1 Hz, 1H), 2.60(dd, J=16.1, 10.1 Hz, 1H), 0.92(s, 9H), 0.22(s, 3H), -0.20(s, 3H) ppm. This was employed in the next step without further purification.

Provenance & Evidence