methyl 2-(dimethylsulfamoyloxy)benzoate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:45.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Methyl 2-{[(dimethylamino)sulfonyl]oxy}benzoate (325.0 mg, 1.253 mmol) was dissolved in 2 ml of 1,4-dioxane and 2 ml of 1M LiOH was added. The resulting solution was shaken overnight at 45° C. The reaction mixture was washed with DCE and separated using a hydrophobic frit. The aqueous layer was acidified to give a white solid which was filtered and dried to afford 244.4 mg (80% yield) of 2-{[(dimethyl-amino)sulfonyl]oxy}benzoic acid. The reaction mixture was washed with DCE separated to give a white solid which was filtered dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Dimethylaminosulphonyl chloride (17.2 g)was added to a mixture of methyl salicylate (15.2 g) and potassium carbonate (27.6 g) in acetonitrile. The mixture was stirred at room temperature for 1 hour. TDA-1 (2.0 g) was added and the mixture stirred at room temperature for 24 hours. The mixture was filtered and the filtrate was evaporated to dryness. The residue was dissolved in dichloromethane, washed with water, dried (MgSO4) and filtered. The filtrate was evaporated to dryness and the residue was triturated with ether. The solid was filtered off and purified by chromatography eluted with dichloromethane to give methyl 2-(dimethylaminosulphonyloxy)benzoate (17.4 g) as a white solid m.p. 75.5°-76.5° C. the mixture stirred at room temperature for 24 hours The mixture was filtered the filtrate was evaporated to dryness The residue was dissolved in dichloromethane washed with water dried (MgSO4) filtered The filtrate was evaporated to dryness the residue was triturated with ether The solid was filtered off purified by chromatography eluted with dichloromethane