Ammonium dithiocarbamate → HCID 178459667, compound

Participants

Reaction Steps

To a solution of allyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(chloroacetyl)-2,5-dihydro-1H-pyrrole-1-carboxylate (163 mg, 0.44 mmol) in methanol (2 ml) were added at 0–5° C. thioisonicotinamide (2 mg) and ammonium dithiocarbamate (72 mg, 0.65 mmol). The reaction mixture was raised to room temperature and stirred for 40 minutes. The mixture was stirred at 65–70° C. for 30 minutes and then at 75–85° C. for 1 hour. The solvent was removed in vacuo. To the solution was added ethyl acetate and the solution was separated with a separating funnel. The aqueous layer was extracted with ethyl acetate. The organic layer was washed twice with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed in vacuo and the residue was recrystallized from ethyl acetate/hexane to give allyl (2S)-2-({[tert-butyl(dimethyl)silyl]oxy}methyl)-3-(2-mercapto-1,3-thiazol-4-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (70.5 mg, 39%).

Provenance & Evidence