Diethyl Ether → 1-[(3-Furanylcarbonyl)amino]cyclohexanecarboxylic acid

HRID 1851798Notes

Reaction equation

HRID 1851798 reaction equation
[OH-].[Na+].C[O:4][C:5]([C:7]1([NH:13][C:14]([C:16]2[CH:20]=[CH:19][O:18][CH:17]=2)=[O:15])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]1)=[O:6].CCOCC>O1CCCC1>[O:18]1[CH:19]=[CH:20][C:16]([C:14]([NH:13][C:7]2([C:5]([OH:6])=[O:4])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8]2)=[O:15])=[CH:17]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 324740101-[(3-Furanylcarbonyl)amino]cyclohexanecarboxylic acid methyl ester

Product 1

HCID 246963411-[(3-Furanylcarbonyl)amino]cyclohexanecarboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

450 ml of 2N aqueous sodium hydroxide solution was added to a solution of 75.4 g (300 mmol) of 1-[(3-furanylcarbonyl)amino]cyclohexanecarboxylic acid methyl ester in 450 ml of tetrahydrofuran, and the mixture was refluxed under heating for 3 hours. After ether was added to the reaction solution to wash, the aqueous layer was neutralized by concentrated hydrochloric acid and extracted with ethyl acetate. After the obtained organic layer was washed with saturated brine and it was dried with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure to obtain 68.8 g (97%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 3 hours
  3. washto wash
  4. extractionextracted with ethyl acetate
  5. washAfter the obtained organic layer was washed with saturated brine and it
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-4f8cfb9c02ef49ddb47b99d463adf7d6
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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