Hydrochloric Acid → HCID 72539640, compound

Participants

Reaction Steps

To a stirred solution of the cyclopropylmethyl derivative (119) (0.38 g, 0.72 mmol) in 1:1:1 THF-methanol-H2O (6 ml) was added conc. hydrochloric acid (0.89 ml), then stirred at r for 6.5 h. The reaction mixture was then neutralized using sodium hydrogen carbonate (approx. 0.9 g solid) and concentrated into approx. half the volume. The residue was partitioned between aq. 10% citric acid (40 ml) and dichloromethane (10 ml). The water layer was washed with dichloromethane (3×10 ml), and the combined organic layers were dried (sodium sulfate), filtered and concentrated. Flash chromatography of the residue using stepwise gradient elution (methanol in ethyl acetate 5-10%) gave after concentration of the appropriate fractions the title compound as a colorless foam (0.315 g, 93%). LR-MS: Calcd for C22H34N3O6S: 468. Found: 468 [M+H].

Provenance & Evidence