Cyclopentanol → 2-Cyclopentyloxy-5-methylsulfamoyl-benzoic acid methyl ester

HRID 1352273Notes

Reaction equation

HRID 1352273 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].[CH:17]1(O)[CH2:21][CH2:20][CH2:19][CH2:18]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: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][CH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

6

Reactant 4

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 97268Di-tert-butyl azodicarboxylateHCID 230467632-Hydroxy-5-methylsulfamoyl-benzoic acid methyl ester

Product 1

HCID 588633522-Cyclopentyloxy-5-methylsulfamoyl-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 2.85 mmol 2-hydroxy-5-methylsulfamoyl-benzoic acid methyl ester, 3.14 mmol cyclopentanol and 3.28 mmol triphenylphosphine in 10 ml THF was added 3.14 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 2:3) to afford the title compound as a colourless oil. MS (m/e): 312.1 ([M−H]−, 100%)

Workup

  1. concentrationThe mixture was then concentrated in vacuo
  2. customThe residue was chromatographed on silica gel (eluant: ethyl acetate/heptane 2:3)

Sources & evidence

ORD record
ord-82ae05b80aa6429fb6166fc99951c15a
Source dataset
uspto-grants-2007_05
Patent number
US07220744B2

Reaction notes

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