Sodium Carbonate → HCID 66810793, compound

Participants

Reaction Steps

A solution of 2-cyanoethyl 1-{[(α-benzoylbenzyloxy)carbonyl]aminomethyl}-1-cyclohexane acetate (9) (115 mg, 0.248 mmol) in 4 mL of CH2Cl2 was added to a mixture of mCPBA (77%, 111 mg, 0.497 mmol) and Na2CO3 (52.7 mg, 0.497 mmol) at room temperature. The resulting suspension was stirred at room temperature with TLC monitoring. After completion of the reaction (about 8 hours) the reaction mixture was diluted with CH2Cl2, washed with saturated NaHCO3 solution and brine and dried over Na2SO4. After concentration in vacuo the residue was purified on silica gel (40% ethyl acetate in hexane) to afford 89 mg (75%) of the title compound. 1H NMR (CDCl3): δ 8.08 (2H, dd, J=6.8, 1.6 Hz); 7.91 (1H, s); 7.63-7.54 (3H, m); 7.44-7.40 (5H, m); 5.42 (1H, t, J=6.4 Hz); 4.22 (2H, t, J=6.2 Hz); 3.25 (2H, dd, J=6.4, 4.6 Hz); 2.65 (2H, t, J=6.2 Hz); 2.35 (2H, s); 1.53-1.37 (10H, m). 13C NMR (CDCl3): δ 172.11; 164.73; 154.75; 136.29; 133.70; 130.18; 129.85; 129.63; 128.85; 128.68; 126.85; 117.11; 91.41; 58.94; 47.93; 10.06; 38.09; 34.15; 26.00; 21.55; 18.16.

Provenance & Evidence