Hydrochloric Acid → (4-Sulfamoylphenoxy)acetic acid methyl ester

HRID 1914716Notes

Reaction equation

[H-].[Na+].[C:3]([O:7][CH3:8])(=[O:6])[CH2:4][OH:5].F[C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1.Cl>CN(C=O)C>[CH3:8][O:7][C:3](=[O:6])[CH2:4][O:5][C:10]1[CH:15]=[CH:14][C:13]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:12][CH:11]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a stirred suspension of NaH (2.8 g, 0.07 mol, 50% in mineral oil) in DMF (50 mL) is added dropwise methyl glycolate (5.5 g, 0.06 mol) over a period of 10 min. The mixture is heated up to 50° C. for 3 h and cooled down to room temperature. 4-Fluorobenzenesulfonamide g, 0.0114 mol) is added portionwise. After stirring at 50° C. for 10 h, the reaction mixture is cooled down and poured into ice-water containing HCl. The product is extracted with DCM (2×100 mL). The combined organic phase is washed with water and dried over Na2SO4. The solvent is evaporated under reduced pressure and the residue is purified by chromatography (silica gel, 60-120 mesh) with chloroform/methanol (9/1) as eluent to afford 900 mg (32%) of the title compound as a solid. 1H NMR (CDCl3, 400 MHz) δ 7.68-721 (m, 2H), 7.10-7.12 (m, 2H), 6.45 (br s, 2H), 4.51 (s, 2H), 3.86 (s, 3H).

Workup

temperaturecooled down to room temperature
addition0.0114 mol) is added portionwise
temperaturethe reaction mixture is cooled down
extractionThe product is extracted with DCM (2×100 mL)
washThe combined organic phase is washed with water
dry with materialdried over Na2SO4
customThe solvent is evaporated under reduced pressure
customthe residue is purified by chromatography (silica gel, 60-120 mesh) with chloroform/methanol (9/1) as eluent

Sources & evidence

ORD record: ord-b50a7ae7e8624e1a8167272d0cc12ba3
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08614215B2

Reaction notes

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