Sulfamic Acid → 2-(3-Methyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester

HRID 1692619Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([CH3:24])[C:17]=1[CH:25]=[O:26].S(=O)(=O)([OH:30])N.[O-]Cl=O.[Na+]>O.C1COCC1.CS(C)=O.O.CCOC(C)=O>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[C:8]([O:10][CH3:11])[C:7]([CH3:12])=[C:6]([O:13][CH3:14])[C:5]=1[O:15][C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([CH3:24])[C:17]=1[C:25]([OH:30])=[O:26]

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 2-(3-methyl-2-Formyl-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (1 mmol) and sulfamic acid (3 mmol) in 7 mL of H2O:THF:DMSO (20:10:1) at 0° C. was treated with NaClO2 (3 mmol) in 1 mL of H2O. The reaction mixture was stirred for 20 min at 0° C. The reaction was diluted with EtOAc (30 mL), washed with saturated aqueous NH4Cl (2×15 mL) and saturated brine, and dried (Na2SO4). Evaporation of the solvents under reduced pressure and further purification by column chromatography gave 2-(3-methyl-2-carboxy-5-methoxy-phenoxy)-3,5-dimethoxy-4-methyl-benzoic acid methyl ester (85%).

Workup

washwashed with saturated aqueous NH4Cl (2×15 mL) and saturated brine
dry with materialdried (Na2SO4)
customEvaporation of the solvents
customunder reduced pressure and further purification by column chromatography

Sources & evidence

ORD record: ord-526b25804fba453ea6b0053a18e38069
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08158623B2

Reaction notes

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