Trifluoromethanesulfonic anhydride → HCID 90224123, compound

Participants

Reaction Steps

Sodium imidazolide (86 mg, 0.960 mmol) was added to a solution of racemic 10-(5-chlorofuran-2-yl)-8-(hydroxymethyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]thiazine-2,4(3H,10H)-dione (115 mg, 0.240 mmol) (Example 17) in DCM (24 ml) at 0° C. The mixture was stirred for 30 minutes, then trifluoromethanesulfonic anhydride (0.049 ml, 0.288 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 3 hours. The mixture was diluted with DCM (10 ml) washed with water (30 ml) and brine (30 ml). The organic layer was passed through a hydrophobic frit and evaporated under vacuum. Purification by chromatography on silica, eluting with 0-20% methanol/DCM, afford the title compound as a mixture of diastereomers.

Provenance & Evidence