Trifluoroacetic acid → HCID 86680183, compound

Participants

Reaction Steps

A solution of 3-(2-cyanopropan-2-yl)-N-(4-methyl-3-(2-(tritylthio)acetyl)phenyl)benzamide 114 (0.799 mmol, 475 mg), trifluoroacetic acid (40.4 mmol, 3 mL) and triethylsilane (0.799 mmol, 0.129 mL) in CH2Cl2 (10 mL) was stirred 1 h at room temperature. Evaporated to dryness and purified by chromatography (10% ethyl acetate in CH2Cl2) gave 3-(2-cyanopropan-2-yl)-N-(3-(2-mercaptoacetyl)-4-methylphenyl)benzamide 115 (71 mg, 25%). NMR (400 MHz, CDCl3) 1.79 (s, 6H), 2.51 (s, 3H), 3.93 (d, J=7.4 Hz, 2H), 7.30 (d, J=8.2 Hz, 1H), 7.54 (m, 2H), 7.72 (dq, J=7.8 Hz and 1.2 Hz, 1H), 7.80 (dt, J=7.8 Hz and 1.6 Hz, 1H), 7.90 (br s, 1H), 8.00 (t, J=2.0 Hz, 1H), 8.19 (d, J=2.0 Hz, 1H).

Provenance & Evidence