Sodium Methoxide → HCID 71271219, compound

Participants

Reaction Steps

To a 10 mL reaction vial was added (3aR,5R,6S,7R,7aR)-5-[(acetyloxy)methyl]-2-[(2E)-but-2-enoylamino]-5,6,7,7a-tetrahydro-3aH-pyrano[3,2-d][1,3]thiazole-6,7-diyl diacetate (40.00 mg; 0.10 mmol; 1.00 eq.) in methanol (2.00 ml) followed by sodium methanolate (0.00 ml; 0.01 mmol; 0.10 eq.). The obtained clear solution was stirred at room temperature for 1 h. LCMS showed a strong peak of SM plus desired product and byproduct (m/z=331). After 5 h, LMCS only showed the product's peak. The solution was diluted with 10 mL MeOH before it was transferred into a 50 mL round-bottom flask. Half spoon resin (Dowex 50WX8) was added. The mixture was gently stirred for 10 sec before it was filtered. 30 mL MeOH was used to rinsed the cake. The obtained solution was concentrated and lyophilized to afford 90.6% of the title compound as a white solid.

Provenance & Evidence