反应详情

温度

55 °C

Me3SnOH (736 mg, 4.07 mmol) was added to a 0.020 M solution of methyl ester 15 (260 mg, 0.509 mmol) in dichloroethane (25.0 mL). The reaction mixture was heated to 55° C. for 22 h and then concentrated. Normal-phase HPFC (100:0 to 90:10:1 CH2Cl2:MeOH:AcOH) followed by reverse-phase HPFC (20:80 to 100:0 MeCN:H2O) and lyophilization afforded 90.0 mg (36%) of 16 as an amorphous solid. [α]D23=+51.5 (c=1.0, MeOH). IR: 1088, 1217, 1651, 1735, 2100, 2964 cm−1. 1H NMR (500 MHz, MeOD): δ 0.88-0.94 (m, 9H), 0.97 (app t, 6H, J=6.8), 1.03 (d, 3H, J=6.5), 1.31 (sept, 1H, J=7.4), 1.72-1.81 (m, 1H), 1.82-1.90 (br s, 1H), 100-2.09 (m, 2H), 2.10-2.17 (m, 1H), 2.18-2.28 (m, 1H), 2.31 (app t, 2H, J=7.5), 3.75 (d, 1H, J=9.5), 4.44-4.68 (br s, 1H), 4.77 (d, 1H, J=9.5), 5.48 (d, 1H, J=12.5), 5.58 (d, 1H, J=12.5), 8.24 (s, 1H). 13C NMR (125 MHz, MeOD): δ 10.8, 16.0, 20.3, 20.6, 22.71, 22.73, 26.0, 26.5, 32.0, 36.7, 39.1, 44.1, 64.6, 69.5, 128.5, 149.2, 164.7, 173.58, 173.61, 179.5. HRMS (FAB) calcd for C22H35N5O6SNa (M+Na): 520.2206. Found: 520.2200.

1. concentrationconcentrated