Ethyl Acetate → HCID 71269627, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of compound 1c (28 g, 87 mmol) obtained above in CH3CN (1.5 L) was added DIPEA (68 g, 520 mmol) at 0° C., followed by BOP-Cl (70 g, 275 mmol). The resulting mixture was stirred at 0° C. for 30 min and then warmed to rt overnight. The solid was removed by filtration and the filtrate was concentrated in vacuo. The residue was dissolved in EA, washed with 2N HCl and dried over anhydrous Na2SO4. Concentration in vacuo and purification by CC eluting with PE:EA=1:2 gave compound 1d as a yellow oil (7.0 g, 30% yield). 1H NMR (400 MHz, CDCl3): δ 7.50 (dd, J=7.6, 1.6 Hz, 1H), 7.41-7.34 (m, 2H), 7.28-7.19 (m, 4H), 7.05 (d, J=7.2 Hz, 2H), 5.83 (m, 1H), 4.82 (d, J=14.0 Hz, 1H), 4.61 (d, J=13.6 Hz, 1H), 3.82-3.78 (m, 1H), 3.78-3.67 (m, 1H), 3.58-3.55 (m, 1H), 2.75-2.71 (m, 2H). MS (ESI+): 268 [M+1]+.

Provenance & Evidence