Methyl chloroformate → Methyl-[(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate

Participants

Reaction Conditions

Reaction Steps

To (3aR,5R,6S,7R,7aR)-2-(ethylamino)-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diol (100.00 mg; 0.40 mmol; 1.00 eq.) in dry THF (12 mL) was added N-ethyl-N-isopropylpropan-2-amine (0.09 ml; 0.52 mmol; 1.30 eq.). The mixture was cooled to 0° C. then methyl chloroformate (0.05 ml, 0.60 mmol, 1.50 eq.) was added dropwise. The reaction was stirred at room temperature for 2 h. The desired product was isolated by flash chromatography (KPNH column, 10 to 100% MeOH/DCM) to afford methyl [(3aR,5R,6S,7R,7aR)-6,7-dihydroxy-5-(hydroxymethyl)-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazol-2-yl]ethylcarbamate (19.6 mg, 16%) as a white solid (once lyophilized).

Provenance & Evidence