p-Toluenesulfonic acid → HCID 89515272, compound

Participants

Reaction Steps

2-Acetamido-N-tert-butyl-2-(3,3-dimethoxycyclobutyl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)hexanamide (5.21 g, 11.10 mmol) was dissolved in acetone (110 mL) and treated with p-toluenesulfonic acid (106 mg, 0.56 mmol). The reaction was stirred overnight at room temperature, then diluted with benzene (500 mL) and heptane (250 mL), washed successively with water and saturated aqueous sodium chloride, dried over MgSO4, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with 50-75% ethyl acetate in heptane to afford the desired product (3.40 g, 73%). Rf 0.31 (75% ethyl acetate in heptane). 1H NMR (CDCl3, 300 MHz) δ 6.83 (br s, 1H), 5.84 (br s, 1H), 3.45-3.33 (m, 1H), 3.09-2.82 (m, 6H), 2.02 (s, 3H), 1.54-1.05 (m, 25H), 0.77 (t, J=7.4 Hz, 2H). ESI MS found for C22H39BN2O5 m/z [423.1 (M+1)].

Provenance & Evidence