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

HRID 73826Notes

Reaction equation

HRID 73826 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, it was extracted with ethyl acetate twice. After the organic layer was washed with saturated brine and it was dried with anhydrous magnesium sulfate, 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. extractionwas extracted with ethyl acetate twice
  8. washAfter the organic layer was washed with saturated brine and 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-2721790c5cb84525b87d8b5bce6ac335
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Reaction notes

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