Methanol → 2-Methoxy-5-methylsulfamoyl-benzoic acid methyl ester

HRID 225707Notes

Reaction equation

HRID 225707 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([S:10](=[O:14])(=[O:13])[NH:11][CH3:12])[CH:7]=[CH:6][C:5]=1[OH:15].CO.[C:19]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=O>C1COCC1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:9]=[C:8]([S:10](=[O:14])(=[O:13])[NH:11][CH3:12])[CH:7]=[CH:6][C:5]=1[O:15][CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 230467632-Hydroxy-5-methylsulfamoyl-benzoic acid methyl ester

Product 1

HCID 230467222-Methoxy-5-methylsulfamoyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.04 mmol 2-hydroxy-5-methylsulfamoyl-benzoic acid methyl ester, 2.2 mmol methanol and 2.34 mmol triphenylphosphine in 10 ml THF was added 2.24 mmol di-tert-butyl azodicarboxylate and the mixture was stirred at RT for 2 h. The mixture was then concentrated in vacuo. The residue was chromatographed on silica gel (eluant: ethyl acetate/heptane) to afford the title compound.

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane)

Sources & evidence

ORD record
ord-b7e3139e06bf49369094a64ce9d49a48
Source dataset
uspto-grants-2009_07
Patent number
US07557114B2

Reaction notes

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