Trifluoroacetic acid → HCID 68840776, compound

Participants

Reaction Steps

The product of step 1 was dissolved in methylene chloride (40 mL) and treated with trifluoroacetic acid (20 mL). After stirring for 2.5 hours the reaction was concentrated and the residue was partitioned between methylene chloride and aqueous sodium bicarbonate solution. The organic layer was removed and the aqueous layer was further basified with concentrated ammonium hydroxide (ca., 20 mL) and extracted with additional methylene chloride. The combined organic layers were dried (sodium sulfate) and concentrated. The resulting tacky, golden solid was triturated with diethyl ether and vacuum oven dried to afford 8.34 g (86%) of product as colorless platelets: 1H NMR (CDCl3) δ 9.25 (s, 1H), 7.54-7.48 (m, 2H), 7.26-7.04 (m, 6H), 4.10-3.98 (m, 2H), 3.67 (dd, J=10.4, 5.5 Hz, 1H), 3.35 (dd, J=16.4, 5.5 Hz, 1H), 2.90 (dd, J=16.4, 10.4 Hz, 1H), 2.57 (t, J=7.6 Hz, 2H), 1.64-1.54 (m, 2H), 1.39-1.24 (m, 4H), 0.88 (t, J=6.8 Hz 3H) ppm.

Provenance & Evidence