Triethylamine → HCID 86621602, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of (1R,2R)-2-acetyloxy-1-methylpropyl (2S)-3-(3,4-dihydroxyphenyl)-2-[(tert-butoxy)carbonylamino]propanoate (34) (0.5 g, 1.2 mmol) and ethyl chloroformate (0.3 mL, 3.0 mmol) in anhydrous dichloromethane, triethylamine (0.4 mL, 3.0 mmol) was added at 0° C. The reaction mixture was stirred at 0° C. for 1 hour. The solution was partitioned between dichloromethane and 10% citric acid and washed with water. The organic layer was dried over MgSO4, and concentrated to dryness. Chromatography (25% ethyl acetate in hexane) provided the title compound (35) (0.6 g, 90% yield) as a white, foamy solid. 1H NMR (400 MHz, CDCl3): δ 1.11 (d, J=6.4 Hz, 3H), 1.13 (d, J=6.4 Hz, 3H), 1.34 (t, J=7.2 Hz, 3H), 1.35 (t, J=7.2 Hz, 3H), 1.40 (s, 9H), 2.02 (s, 3H), 3.02 (dd, J=14.0, 6.8 Hz, 1H), 3.07 (dd, J=14.0, 6.8 Hz, 1H), 4.27 (q, H=7.2 Hz, 2H), 4.28 (q, J=7.2 Hz, 2H), 4.51 (dd, J=14.0, 6.8 Hz, 1H), 4.93 (m, 2H), 5.03 (d, J=8.4 Hz, 1H, NH), 7.03 (dd, J=8.0, 2.0 Hz, 1H), 7.06 (d, J=2.0 Hz, 1H), 7.16 (d, J=8.0 Hz, 1H). MS (ESI) m/z 578.1 (M+Na)+.

Provenance & Evidence