Ethyl Acetate → HCID 86681595, compound

Participants

Reaction Steps

To a solution of amine 62 (0.79 g, 2.43 mmol) in THF (20 mL) was added DiPEA (1.2 eq., 2.91 mmol, 482 μL), and benzylchloroformate (1.1 eq., 2.67 mmol, 392 μL) and the mixture was stirred for 4 hours in which a colorless solid precipitated. EtOAc was added and the mixture was extracted with 1 M aq. HCl (2×), sat. aq. NaHCO3 and brine, dried over MgSO4 and concentrated under reduced pressure. The title compound was obtained after column chromatography (10%->75% EtOAc/PE) as a colorless foam (yield: 0.95 g, 2.06 mmol, 85%). 1H NMR (400 MHz, CDCl3): δ=7.33-7.23 (m, 7H), 7.14 (s, 1H), 7.05 (d, J=8.21 Hz, 2H), 5.80 (d, J=8.71 Hz, 1H), 5.04 (dd, J=26.77, 12.39 Hz, 2H), 4.98-4.94 (m, 1H), 3.62 (s, 3H), 3.13 (s, 3H), 3.01 (dd, J=13.65, 5.91 Hz, 1H), 2.85 (dd, J=13.58, 7.35 Hz, 1H), 1.49 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3): δ=171.72, 155.64, 152.64, 137.21, 136.07, 130.35, 129.52, 128.13, 127.69, 127.64, 118.18, 79.88, 66.41, 61.21, 51.95, 37.53, 31.73, 28.05 ppm. [α]D23=+8.1 (c=1, CHCl3). HRMS: calcd. for C24H31N3O6 458.22856 [M+H]+. found 458.22845.

Provenance & Evidence