Trifluoroacetic acid methylene chloride → HCID 67804264, compound

Participants

Reaction Steps

A 159 mg sample of the BOC-protected intermediate from step 1b above was dissolved in 10 mL of 1:1 TFA/methylene chloride and stirred at room temperature for 16 hr. The solvents were removed by evaporation, and excess 10% aqueous NaHCO3 was added. The solution was extracted 3× with methylene chloride, the extract was dried over MgSO4 and the solvent was removed. The residue was purified by column chromatography on silica gel, eluting with 10:1 chloroform:methanol. The product was dissolved in ether and treated with HCl/ether. The white precipitate was filtered off, washed with ether, and dried under vacuum to afford 71 mg of the title product. MS: 223 (M+H)+, 240 (M+NH4)+. NMR (D2O) δ: 1.91-2.36 (m, 4H), 3.39-3.46 (m, 2H), 4.14 (dq, 1H, J=3.3, 8 Hz), 4.27 (dd, 1H, J=7.7, 10.6 Hz), 4.50 (dd, 1H, J=3.3, 10.6 Hz), 7.42-7.46 (m, 1H), 7.59 (t, 1H, 8 Hz), 7.87 (t, 1H, 2.5), 7.95 (ddd, 1H, J=1, 2, 3.3 Hz). Anal. Calcd for C11H15ClN2O3 : C, 51.07; H, 5.84; N, 10.83; Found: C, 51.01; H, 5.88; N, 10.63.

Provenance & Evidence