Trityl chloride → HCID 86681593, compound

Participants

Reaction Steps

To a solution of amine 62 (0.38 g, 1.16 mmol) in DCM (15 mL) was added Et3N (1.2 eq., 1.40 mmol, 195 μL), and tritylchloride (1.2 eq., 1.40 mmol, 0.40 g) and the mixture was stirred for 14 hours. DCM was evaporated under reduced pressure and the residue was dissolved in EtOAc, extracted with 10 mM aq. HCl (2×) and brine, dried over MgSO4 and concentrated under reduced pressure. The title compound was obtained after column chromatography (10%->50% EtOAc/PE) as a colorless foam (yield: 0.61 g, 1.11 mmol, 96%). 1H NMR (400 MHz, CDCl3): δ=7.46 (s, 1H), 7.36 (d, J=7.55 Hz, 6H), 7.22-7.02 (m, 13H), 6.95 (s, 1H), 4.01-3.95 (m, 1H), 3.10 (s, 3H), 2.88 (dd, J=13.31, 5.95 Hz, 1H), 2.73 (dd, J=13.03, 7.26 Hz, 1H), 2.61 (s, 3H), 1.49 (s, 9H) ppm. 13C NMR (100 MHz, CDCl3): δ=174.86, 152.68, 145.93, 136.93, 132.49, 130.36, 128.66, 127.31, 125.82, 118.18, 79.91, 70.58, 59.93, 41.63, 31.92, 28.15 ppm. [α]D23=+75.8 (c=1, CHCl3). HRMS: calcd. for C35H39N3O4 566.30133 [M+H]+. found 566.30120.

Provenance & Evidence