methyl 4-sulfamoylbutanoate

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

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-sulfamoylbutyric acid (2.53 g, 15.1 mmol), methanol (25 ml), trimethylorthoformate (10 ml, approx 5 eq) and polystyrene-bound toluenesulfonic acid (0.58 g) was stirred at 60° C. After 19 h the mixture was decantated from the catalyst and concentrated to yield 2.70 g (99%) of the title ester as an oil. concentrated

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

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

Procedure: To a solution of (1-benzyl-2-methyl-1H-indol-4-yloxy)-acetic acid (5) (0.189 g, 0.64 mmole) in dichloromethane (15 mL), 4-sulfamoyl-butyric acid methyl ester (0.232 g, 1.28 mmole), EDCI (0.122 g, 0.64 mmole) and DMAP (0.078 g, 0.64 mmole) were added. The mixture was stirred at room temperature for 18 h. The dichloromethane was evaporated to half of the original volume and the mixture was washed with water (2×10 mL). The organic layer was separated and evaporated. The residue was purified by column chromatography (10:1 CHCl3:MeOH) to afford intermediate (6) as a solid. Yield: 0.15 g, 51% The dichloromethane was evaporated to half of the original volume the mixture was washed with water (2×10 mL) The organic layer was separated evaporated The residue was purified by column chromatography (10:1 CHCl3:MeOH)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 4-sulfamoylbutyric acid (2.53 g, 15.1 mmol), methanol (25 ml), trimethylorthoformate (10 ml, approx 5 eq) and polystyrene-bound toluenesulfonic acid (0.58 g) was stirred at 60° C. After 19 h the mixture was decantated from the catalyst and concentrated to yield 2.70 g (99%) of the title ester as an oil. concentrated