1,2-Dichloroethane → HCID 53994349, compound

Participants

Reaction Steps

A solution of 1720 mg (3.38 mmol) of Z-Glu-OtBu DCHA in 17 mL of dichloromethane was cooled to 0° C. and treated with 0.448 mL (6.75 mmol, 2.0 equiv) of glycidol, 41.2 mg (0.338 mmol, 0.1 equiv) of DMAP and 970 mg (5.06 mmol, 1.5 equiv) of EDC according to the general procedure for EDC/DMAP esterification. Purification by flash chromatography (30×150 mm silica gel, 35% ethyl acetate/hexane) gave 971 mg (73%) of the title compound: 1H NMR (300 MHz, CD3OD) δ7.38-7.24 (m, 5H), 5.09 (s, 2H), 4.41 (dd, J=2.9, 12.4 Hz, 1H), 4.13-4.09 (overlapping dd, 1H), 3.91-3.84 (overlapping dd, 1H), 3.32-3.16 (m, 1H), 2.80-2.78 (overlapping t, 1H), 2.64-2.61 (overlapping dd, 1H), 2.47 (t, J=7.6 Hz, 2H), 2.20-2.08 (m, 1H), 1.97-1.84 (m, 1H), 1.45 (s, 9H); MS(FAB) 394 (M+1), 338, 294, 260.

Provenance & Evidence