Sodium Hydroxide → 1-[[(2-Furanylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid

HRID 448731Notes

Reaction equation

HRID 448731 reaction equation
C[O:2][C:3]([C:5]1([NH:11][C:12]([O:14][CH2:15][C:16]2[O:17][CH:18]=[CH:19][CH:20]=2)=[O:13])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:4].[OH-].[Na+]>O1CCCC1>[O:17]1[CH:18]=[CH:19][CH:20]=[C:16]1[CH2:15][O:14][C:12]([NH:11][C:5]1([C:3]([OH:4])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]1)=[O:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 576728881-[[(2-Furanylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid methyl ester

Product 1

HCID 576728901-[[(2-Furanylmethoxy)carbonyl]amino]cyclohexanecarboxylic acidYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

28.13 g (0.1 mol) of 1-[[(2-furanylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid methyl ester was added to a mixture solution of 150 ml of 2N aqueous sodium hydroxide solution and 200 ml of tetrahydrofuran, and the mixture was heated under reflux for 18 hours. After the solvent was distilled off, water was added to the residue and the mixture was washed with diethyl ether. After potassium hydrogensulfate was added to the aqueous layer to acidify it, the mixture was extracted with ethyl acetate twice. After the organic layer was washed with saturated brine, it was dried with anhydrous magnesium sulfate, and thereafter the solvent was distilled off under reduced pressure. Diisopropyl ether was added to the residue, and the mixture was stirred for 18 hours. The obtained crystal was collected by filtration to obtain 19.89 g (74%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. distillationAfter the solvent was distilled off
  4. additionwater was added to the residue
  5. washthe mixture was washed with diethyl ether
  6. additionAfter potassium hydrogensulfate was added to the aqueous layer
  7. extractionthe mixture was extracted with ethyl acetate twice
  8. washAfter the organic layer was washed with saturated brine, it
  9. dry with materialwas dried with anhydrous magnesium sulfate
  10. distillationthe solvent was distilled off under reduced pressure
  11. additionDiisopropyl ether was added to the residue
  12. filtrationThe obtained crystal was collected by filtration

Sources & evidence

ORD record
ord-a18e07a2d3c14e4c9722f8eacc456ff3
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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