Chlorosuccinimide → HCID 88180221, compound

Participants

Reaction Steps

N-chlorosuccinimide (117 mg, 0.9 mmol) is added to a solution of compound (45) (200 mg, 0.4 mmol in 5 ml of DMF). After it had been stirred (at room temperature for 16 h), the solution is added to a mixture of CH2Cl2 /5% aq. NaHCO3 (50 ml, 9:1). The organic phase is separated off, washed with water, dried over Na2SO4, filtered and evaporated. The evaporated residue is dissolved in CH2Cl2 and this solution is chromatographed on silica gel (column: 5×20 cm, CH2Cl2 /acetone, 95:5). The main zone is separated off. Colorless crystals (149 mg, 72%) are obtained after evaporating off the solvent and crystallizing from cyclohexane. Melting point: 127-128° C. 1H-NMR ([D6 ] DMSO): δ=1.01 (dd, CH3), 1.14 (d, J=7.0, CH3), 2.44, 2.47, 2.60, 3.53 (4 m, CH and Hα,β --C(2')), 4.05 (s, OCH3), 4.17 (m, H--C(5')), 4.30 (m, H--C(4')), 5.56 (m, H--C(3')), 6.41 (m, H--C(1')), 9.44 (d, J=9.1, NH), 10.94 (d, J=9.8, HCO). Anal. calculated for C21H26Cl2N4O7 (517.4): C, 48.75, H, 5.07, N, 10.83; found: C, 49.04, H, 5.09, N, 10.66.

Provenance & Evidence