3-(hydroxymethyl)benzenesulfonamide

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

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

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

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

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

Procedure: A solution of 3(hydroxymethyl)benzenesulfonamide (670 mg) in DMF (20 ml) under nitrogen was treated with sodium hydride (315 mg, 60% in oil) and the mixture was stirred at 20° for 15 min. The mixture was then treated with 2-(trimethylsilyl)ethoxymethyl chloride (1.27 ml) and the mixture was stirred at 20° for 1 h. Phosphate buffer solution (50 ml, pH6.5) was added and the mixture was extracted with EtOAc. The extract was washed with water, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue. The residue was purified by chromatography on flash silica gel (40 mm diameter column). Elution with EtOAc-cyclohexane (3:7) gave the title compound (985 mg). LCMS RT=3.84 min. the mixture was stirred at 20° for 1 h the mixture was extracted with EtOAc The extract was washed with water dried (Na2SO4) the solvent evaporated in vacuo to give a residue The residue was purified by chromatography on flash silica gel (40 mm diameter column) Elution with EtOAc-cyclohexane (3:7)

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

Procedure: A solution of 3(hydroxymethyl)benzenesulfonamide (670 mg) in DMF (20 ml) under nitrogen was treated with sodium hydride (315 mg, 60% in oil) and the mixture was stirred at 20° for 15 min. The mixture was then treated with 2-(trimethylsilyl)ethoxymethyl chloride (1.27 ml) and the mixture was stirred at 20° for 1 h. Phosphate buffer solution (50 ml, pH6.5) was added and the mixture was extracted with EtOAc. The extract was washed with water, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue. The residue was purified by chromatography on flash silica gel (40 mm diameter column). Elution with EtOAc-cyclohexane (3:7) gave the title compound (985 mg). LCMS RT=3.84 min. the mixture was stirred at 20° for 1 h the mixture was extracted with EtOAc The extract was washed with water dried (Na2SO4) the solvent evaporated in vacuo to give a residue The residue was purified by chromatography on flash silica gel (40 mm diameter column) Elution with EtOAc-cyclohexane (3:7)

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

Procedure: Sodium hydride (60% oil dispersion, 0.177 g) was added to 3-hydroxymethylbenzenesulfonamide (0.77 g) with stirring in DMF (15 ml) under nitrogen at 21°. After 10 min, isopropyl iodide (0.45 ml) was added followed by a further 0.3 ml after 1 h. After an additional 2 h more isopropyl iodide (0.2 ml) was added. After 3 days more sodium hydride oil dispersion (0.08 g) was added. After another day, the solution was poured into water acidified with 2M hydrochloric acid and the product was extracted with ethyl acetate twice. The combined extracts were washed with brine and evaporated to an oil. This oil was loaded onto a column of silica gel (60 g) and the column was eluted successively with 30%, 50% and 70% ethyl acetate in 40-60 petroleum ether to give the title compound (0.527 g) LCMS RT=2.22 min. followed by a further 0.3 ml after 1 h After another day the product was extracted with ethyl acetate twice The combined extracts were washed with brine evaporated to an oil the column was eluted successively with 30%, 50% and 70% ethyl acetate in 40-60 petroleum ether

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

Procedure: Sodium hydride (60% oil dispersion, 0.315 g) was added to 3-hydroxymethylbenzenesulfonamide (0.67 g) with stirring in DMF (20 ml) under nitrogen at 20°. After 15 min, 2-(trimethylsilyl)ethoxymethyl chloride (1.27 ml) was added and stirring was continued for 1.5 h. pH 6.4 Phosphate buffer and ethyl acetate were added. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were washed twice with brine, dried (MgSO4) and evaporated to an oil. This oil in dichloromethane was loaded onto a column of silica gel (75 g) set up in 10% ethyl acetate in 40-60 petroleum ether. The column was run with this, then 20%, 30% and 50% ethyl acetate in 40-60 petroleum ether to give the title compound (0.74 g) LCMS RT=4.00 min. was continued for 1.5 h. The aqueous layer was extracted twice with ethyl acetate the combined organic layers were washed twice with brine dried (MgSO4) evaporated to an oil

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

Procedure: Sodium hydride (60% oil dispersion, 0.315 g) was added to 3-hydroxymethylbenzenesulfonamide (0.67 g) with stirring in DMF (20 ml) under nitrogen at 20°. After 15 min, 2-(trimethylsilyl)ethoxymethyl chloride (1.27 ml) was added and stirring was continued for 1.5 h. pH 6.4 Phosphate buffer and ethyl acetate were added. The aqueous layer was extracted twice with ethyl acetate and the combined organic layers were washed twice with brine, dried (MgSO4) and evaporated to an oil. This oil in dichloromethane was loaded onto a column of silica gel (75 g) set up in 10% ethyl acetate in 40-60 petroleum ether. The column was run with this, then 20%, 30% and 50% ethyl acetate in 40-60 petroleum ether to give the title compound (0.74 g) LCMS RT=4.00 min. was continued for 1.5 h. The aqueous layer was extracted twice with ethyl acetate the combined organic layers were washed twice with brine dried (MgSO4) evaporated to an oil

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

Procedure: 3-(Aminosulfonyl)benzoic acid (2.18 g) was stirred with ice-water cooling and under nitrogen while borane-THF complex (32.5 ml) was added dropwise over 15 min. After 2 h at 22° further borane-THF complex (16 ml) was added. After a further 2 h the mixture was cooled with ice-water and methanol (40 ml) was added dropwise. After 15 min 2M hydrochloric acid (90 ml) was added and the mixture was left to stand at 21° overnight. The solution was extracted 3 times with ethyl acetate and the organic layers were combined and washed twice with brine, dried (MgSO4) and concentrated. This solution was loaded onto a column of silica gel (200 g) and the column was run with ethyl acetate and then 10% methanol in ethyl acetate to give the title compound (1.595 g), LCMS RT=0.83 min. was added dropwise over 15 min After 2 h at 22° further borane-THF complex (16 ml) was added was added dropwise the mixture was left The solution was extracted 3 times with ethyl acetate washed twice with brine dried (MgSO4) concentrated

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

Procedure: A solution of 3-(hydroxymethyl)benzenesulfonamide (670 mg) in DMF (20 ml) under nitrogen was treated with sodium hydride (315 mg, 60% in oil) and the mixture was stirred at 20° for 15 min. The mixture was then treated with 2-(trimethylsilyl)ethoxymethyl chloride (1.27 ml) and the mixture was stirred at 20° for 1 h. Phosphate buffer solution (50 ml, pH6.5) was added and the mixture was extracted with EtOAc. The extract was washed with water, dried (Na2SO4) and the solvent evaporated in vacuo to give a residue. The residue was purified by chromatography on flash silica gel (40 mm diameter column). Elution with EtOAc-cyclohexane (3:7) gave the title compound (985 mg). LCMS RT=3.84 min. the mixture was stirred at 20° for 1 h the mixture was extracted with EtOAc The extract was washed with water dried (Na2SO4) the solvent evaporated in vacuo to give a residue The residue was purified by chromatography on flash silica gel (40 mm diameter column) Elution with EtOAc-cyclohexane (3:7)

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

Procedure: A solution of 3-(hydroxymethyl)benzenesulfonamide (307 mg, 1.64 mmol) in acetone (16 mL) was added to a round bottom flask containing MnO2 (1.43 g, 16.4 mmol). The mixture was stirred for 50 hours until the starting material was consumed, then filtered though a pad of celite. The filtrate was evaporated to afford the product (232 mg, 76%) as a white solid. MS (ES+) m/z 186 [M+H]+. was consumed filtered though a pad of celite The filtrate was evaporated