Methanol → HCID 17910259, compound

HRID 1953269Notes

Reaction equation

HRID 1953269 reaction equation
[CH3:1][NH:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([C:9]2([CH2:15][C:16]([OH:18])=[O:17])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)=[O:8])=[CH:5][C:4]=1[N+:21]([O-:23])=[O:22].[CH3:24]O>O1CCCC1>[CH3:24][O:17][C:16](=[O:18])[CH2:15][C:9]1([C:7](=[O:8])[C:6]2[CH:19]=[CH:20][C:3]([NH:2][CH3:1])=[C:4]([N+:21]([O-:23])=[O:22])[CH:5]=2)[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]1

Participants

4

Reactant 2

HCID 887MethanolHCID 23302379HCID 23302379, compound

Product 1

HCID 17910259HCID 17910259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.9 g (0.015 mol) of [1-(4-methylamino-3-nitro-benzoyl)-cyclohexyl]-acetic acid are dissolved in 100 ml tetrahydrofuran and after the addition of 2.4 g (0.015 mol) of N,N'-carbonyldiimidazole the mixture is refluxed for 15 minutes. After concentration of the solution and addition of 30 ml methanol the mixture is refluxed for 3 hours. The solvent is distilled off, the residue chromatographed on silica gel and eluted with methylene chloride+methanol (1-5%). The desired fractions are combined and concentrated by evaporation.

Workup

  1. temperatureis refluxed for 15 minutes
  2. temperatureis refluxed for 3 hours
  3. distillationThe solvent is distilled off
  4. customthe residue chromatographed on silica gel
  5. washeluted with methylene chloride+methanol (1-5%)
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-3cbd1d38fee64fc591ef5fc8295bc57b
Source dataset
uspto-grants-2000_09
Patent number
US06114532

Reaction notes

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