4-Methoxybenzyl alcohol → 2-(4-Methoxy-benzyloxy)-5-sulfamoyl-benzoic acid methyl ester

HRID 2251278Notes

Reaction equation

HRID 2251278 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[CH:7]=[CH:6][C:5]=1[OH:14].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]O)=[CH:20][CH:19]=1.C1(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:15])[C:4]1[CH:9]=[C:8]([S:10](=[O:13])(=[O:12])[NH2:11])[CH:7]=[CH:6][C:5]=1[O:14][CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1

Participants

6

Reactant 4

HCID 77384-Methoxybenzyl alcoholHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 14266941Methyl 2-hydroxy-5-sulfamoylbenzoate

Product 1

HCID 690375322-(4-Methoxy-benzyloxy)-5-sulfamoyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 4.8 mmol 2-hydroxy-5-sulfamoyl-benzoic acid methyl ester, 5.2 mmol 4-methoxybenzyl alcohol and 5.2 mmol triphenylphosphine in 8 ml THF was added 5.2 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 gradient) to afford the title compound. MS (m/e): 350.2 ([M−H]−, 100%)

Workup

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

Sources & evidence

ORD record
ord-1adcf4f2e79e4bb9a5c667baa7ee61fc
Source dataset
uspto-grants-2008_01
Patent number
US07319099B2

Reaction notes

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