HCID 86716476, compound → HCID 2205350, compound

Participants

Reaction Steps

A mixture of N1-n-butyl-N2-(5-(tert-butyldiphenylsilyloxy)pentyl)oxalamide (65 mg, 0.14 mmol) and n-tetrabutylammonium fluoride (0.41 mL, 1 M soln, 0.42 mmol) in dry THF solution was stirred at room temperature under an argon atmosphere for 12 h. All volatiles were evaporated in vacuo, the residue was dissolved in EtOAc (30 mL) and the organic layer was washed with water (10 mL), brine (15 mL), dried and evaporated. Purification of the residue via SiO2 column chromatography using EtOAc/hexanes (1:2) as eluent gave the title compound (30 mg, 92%) as a colorless solid, mp 136-137° C. TLC: 50% EtOAc/hexane, Rf˜0.28; 1H NMR (300 MHz) δ 7.65 (br s, NH, 1H), 7.60 (br s, —NH, 1H), 3.65 (t, J=6.0 Hz, 2H), 3.35-3.25 (m, 4H), 1.90 (br s —OH, 1H), 1.60-1.50 (m, 6H), 1.40-1.35 (m, 4H), 0.92 (t, J=7.3 Hz, 3H); 13C NMR (100 MHz) δ 160.25, 160.10, 62.70, 39.80, 39.65, 32.40, 31.45, 29.20, 23.25, 20.20, 13.85. HRMS calcd for C11H23N2O3 [M+1]+ 231.1709, found 231.1701.

Provenance & Evidence