Triethylamine → (4-phenylphenyl)-methyl-N-[(2R*,3R*)-2-ethyl-4-oxo-oxetan-3-yl]-carbamate

Participants

Reaction Conditions

Reaction Steps

Under nitrogen atmosphere, to a stirred mixture of (2R*,3R*)-3-hydroxy-2-[(4-phenylphenyl)-methoxycarbonylamino]-pentanoic acid and (2R*,3S*)-3-hydroxy-2-[(4-phenylphenyl)-methoxycarbonylamino]-pentanoic acid (0.193 g, 0.56 mmol) in dry CH2Cl2 (25.0 mL), at 0° C., Et3N (0.235 mL, 1.69 mmol) and subsequently TBTU (0.217 g, 0.67 mmol) were added. The mixture was left stirring at 0° C. for 1 h and at rt for 15 h. The organics were then removed under reduced pressure, and the resulting crude product purified by column chromatography, using a Teledyne ISCO apparatus, eluting with Cy/AcOEt (from 90:10 to 80:20) to afford the pure title compound (0.089 g, 57%), as pure anti diastereoisomer, as white solid. MS (ESI) m/z: 343 [M−NH4]+; (ESI) m/z: 324 [M−H]−. 1H NMR (DMSO-d6) δ 0.92 (t, J=7.38 Hz, 3H), 1.68-1.94 (m, 2H), 4.49-4.60 (m, 1H), 4.76 (dd, J=4.32, 8.08 Hz, 1H), 5.12 (s, 2H), 7.33-7.42 (m, 1H), 7.42-7.53 (m, 4H), 7.62-7.76 (m, 4H), 8.25 (d, J=8.09 Hz, 1H).

Provenance & Evidence