3-Sulfamoylbenzoic acid → 3-(Hydroxymethyl)benzene-1-sulfonamide

Temperature

0 °C

To a solution of 3-(aminosulfonyl)benzoic acid (Fluorochem) (150 mg, 0.746 mmol) in THF (1 mL) was added dropwise at 0° C. Borane-THF complex (3.73 mL, 3.73 mmol). The resulting solution was stirred 10 min at 0° C., and then at room temperature overnight. The reaction mixture was carefully quenched with 10 mL of water at 0° C. The reaction mixture was diluted with 30 mL of EtOAc and 20 ml of water. The aqueous layer was further extracted with 30 mL of EtOAc. The combined organic solutions were washed with brine (30 mL), dried over an hydrophobic frit and concentrated under reduced pressure. The residue was loaded in dichloromethane to a silica cartridge (20 g), and purified by chromatography on Flashmaster using a 0-100% ethyl acetate-dichloromethane over 40 min. The appropriate fractions were combined and evaporated in vacuo to give the title compound (86.4 mg, 62%) as a gum. LCMS (System A) RT=0.41 min, ES+ve m/z 188 (M+H)+.

1. customat room temperature
2. customovernight
3. customThe reaction mixture was carefully quenched with 10 mL of water at 0° C
4. additionThe reaction mixture was diluted with 30 mL of EtOAc and 20 ml of water
5. extractionThe aqueous layer was further extracted with 30 mL of EtOAc
6. washThe combined organic solutions were washed with brine (30 mL)
7. customdried over an hydrophobic frit
8. concentrationconcentrated under reduced pressure
9. custompurified by chromatography on Flashmaster
10. customover 40 min
11. customevaporated in vacuo

ORD record

ord-d382fd1e8c6949baaee1cb69c0ee1293

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304446B2