Trifluoroacetic acid → HCID 86589155, compound

Participants

Reaction Steps

N-(tert-butoxycarbonyl)-L-alanyl-N1-isobutyl-L-valinamide (247 mg, 0.72 mmol) is stirred for 30 min under nitrogen with 1 mL of trifluoroacetic acid and 3 mL of dichloromethane. It is concentrated on a rotary evaporator. To the residue is added 2 mL of saturated sodium bicarbonate (pH=8). The product is diluted with 100 mL of ethyl ether. The aqueous salt is siphoned out and anhydrous sodium sulfate is added. The solution is filtered through glass wool and concentrated to 136 mg of the title compound as an off-white solid. NMR (MeOD)-d3 δ 4.66 (bs) 4.16 (d, J=8 Hz, 1H), 4.00 (q, J=7 Hz, 1H), 3.07 (dd, 1H), 2.98 (dd, 1H), 2.05 (m, 1H), 1.79 (m, 1H), 1.49 (d, J=7 Hz, 3H), 0.99 (d, J=7 Hz, 6H) 0.93 (d, J=7 Hz, 6H). HRMS (ESI) calcd for C12H25N3O2+H1 244.2025, found 244.2023.

Provenance & Evidence