Sodium Iodide → HCID 86654431, compound

Participants

Reaction Conditions

Reaction Steps

To acid 20 (40.0 mg, 0.18 mmol) in benzene (0.3 mL) was added 18-crown-6 (48.0 mg, 0.18 mmol) and K2CO3 (23.1 mg, 0.18 mmol). The mixture was stirred for 1 h and alcohol 18 (41.0 mg, 0.15 mmol) was added followed by NaI (27.2 mg, 0.18 mmol). The reaction mixture was heated to 50° C. for 3 h, and then cooled. The mixture was diluted with CH2Cl2 (1.0 mL), washed with saturated NaHCO3 solution (3.0 mL), extracted with CH2Cl2 (3×3.0 mL), drying over anhydrous Na2SO4, and concentration under reduced pressure. FCC on silica gel with 40% EtOAc in hexane yielded ester 21 (41.8 mg, 68.0%) as a cream oil. 1H NMR (400 MHz, CDCl3): δ 8.44 (1H, s), 7.62 (3H, m), 7.46 (1H, m), 7.37 (1H, m), 7.09 (1H, t, J=5.2), 6.59 (1H, d, J=15.7), 6.42 (1H, m), 5.16 (2H, d, J=3.8), 4.34 (2H, m), 3.03 (2H, t, J=7.1), 2.80 (2H, t, J=7.0), 2.03 (1H, bs); 13C NMR: δ 171.6, 159.7, 150.0, 149.6, 148.8, 135.3, 131.1, 130.6, 130.3, 129.3, 128.8, 128.2, 121.3, 120.7, 62.5, 34.1, 33.7, 33.2; HRFABMS m/z 407.0741 (+1.4 ppm/+0.6 mmu) [M+H+] (calcd for C18H19N2O5S2, 407.0735).

Provenance & Evidence