Thionyl Chloride → HCID 19019105, compound

Participants

Reaction Steps

Compound 25 (110 mg, 0.22 mmol) was refluxed for 1 h with thionyl chloride (1 mL) in chloroform (4 mL). The volatile material was removed in vacuo, and the residue was basified with aqueous Na2CO3 (pH 10) and washed immediately with ether to completely remove the non polar impurity (TLC CHCl3 /CH3OH/NH4OH: 9/1/0.1, Rf 0.4). The product was extracted into CHCl3 from the cold aqueous phase and the combined CHCl3 layers were concentrated in vacuo and acidified using ether/HCl. The precipitate was dried in vacuo to yield 29 mg of 26 (25%) as a white solid: mp 188°-190° C.; 1H NMR (D20, HCl salt) δ 3.00-4.00 (m, 14 H), 7.50-7.70 (m, 3 H), 7.70-7.90 (m, 3 H), 8.40 (s, 1 H); MS (CI/NH3) m/e 400 (MH+), 212 (base), 364, 338. FAB mass spectroscopy showed peaks at mass 438 (M+ K), 422 (M+ Na), 400 (M+ H), 364, 329, 307, 289, 211, 154, and 136. The salt was stable upon storage at -20 ° C. for at least 6 months.

Provenance & Evidence