1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 10239105, compound

Participants

Reaction Conditions

Reaction Steps

(5R)-3-[4-(1,1-Dioxo-3,6-dihydro-2H-thiopyran-4-yl)-3-fluorophenyl]-5-[4-(2,2-dibromoethenyl)-1,2,3-triazol-1-ylmethyl]oxazolidin-2-one (Example 25) (0.5 g, 0.87 mmol) was dissolved in DMSO (87 ml) and cooled to 15° C. 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) (0.262 ml, 1.75 mmol), dissolved in DMSO (1.7 ml), was added drop wise under stirring over 30 minutes. The temperature was maintained at 15–18° C. and after 6 hours more DBU (0.125 ml, 0.83 mmol) was added drop wise via a syringe and the resulting solution stirred for another 30 minutes. The reaction was quenched with cold aqueous HCl (0.5 M), extracted with dichloromethane, washed with water and dried over sodium sulfate. Chromatography on silica gel with hexanes/acetone (1.5:1 to 1:1) gave 108 mg (25%) of the title product as a colourless solid.

Provenance & Evidence