Trifluoroacetic anhydride → HCID 46701211, compound

Participants

Reaction Steps

The final compound was prepared by adding triethylamne (80.0 mg, 0.78 mmol) to a stirred solution of Step 2 product (121 mg, 0.263 mmol) dissolved in dry DCM (5 ml) follwed by addition of triflouroacetic anhydride (84 mg, 0.395 mmol) at 0° C., under nitrogen atmosphere and the reaction mixture stirred for 1 h. The reaction mixture was then extracted with CHCl3 and the combined organic layers washed with water, brine, dried (Na2SO4), filtered and concentrated under vaccum. The crude product was purified by silica gel column chromatography using 2% acetone in chloroform to give 79 mg of the product of off-white solid; IR (KBr) 2959, 2243, 1573, 1455, 1263, 743 cm−1; 1H NMR (300 MHz, DMSO-d6) δ 1.62-1.68 (m, 4H), 1.78-1.89 (m, 4H), 3.86 (s, 3H), 4.89 (br s, 1H), 6.90 (d, J=7.8 Hz, 1H), 7.03 (t, J=7.8 Hz, 1H), 7.11 (d, J=7.8 Hz, 1H), 7.23-7.28 (m, 1H), 7.35-7.44 (m, 2H), 7.59 (d, J=7.8 Hz, 1H), 7.87 (d, J=9.3 Hz, 2H), 8.06 (d, J=9.0 Hz, 1H), 8.19 (d, J=15.9 Hz,1H); APCI-MS (m/z) 438.21 (M+H)+.

Provenance & Evidence