Chlorosuccinimide → HCID 15218404, compound

Participants

Reaction Steps

N-Chlorosuccinimide (87 mg, 0.67 mmol) is added to a solution of compound (18) (300 mg, 0.67 mmol in 5 ml of DMF). After it has been stirred (at room temperature for 20 h), the solution is added to a mixture of CH2Cl2/5% aq. NaHCO3 (50 ml, 9:1). The organic layer 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 concentrated, and n-hexane is added to the residue. The precipitated colorless crystals (230 mg, 71%) are isolated. Melting point: 119-120° C. 1H-NMR ([D6] DMSO): δ=1.09 (d, J=7.0, CH3), 1.15 (d, J=6.9, CH3), 2.45, 2.60, 2.63, 2.89 (4m, CH and Hα,β-C(2′)), 4.06 (s, OCH3), 4.18 (m, H—C(5′)), 4.28 (m, H—C(4′)), 5.35 (m, H—C(3′)), 6.47 (m, H—C(1′)), 7.58 (s, H—C(6)), 9.45 (d, J=8.9, NH), 10.84 (d, J=9.6, HCO). Anal. calculated for C21H27CIN4O7 (482.9): C 52.23, H 5.64, N 11.60; found: C 52.51, H 5.69, N 11.65.

Provenance & Evidence