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

HRID 1627440Notes

Reaction equation

HRID 1627440 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 heated under reflux for 3 hours. After ether was added to the reaction solution to wash it, the aqueous layer was neutralized by concentrated hydrochloric acid and extracted with ethyl acetate. After the obtained organic layer was washed with saturated brine, 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 heated
  2. temperatureunder reflux for 3 hours
  3. washto wash it
  4. extractionextracted with ethyl acetate
  5. washAfter the obtained organic layer was washed with saturated brine, it
  6. dry with materialwas dried with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-2800bd7017dd44318ad3c0b2484815fb
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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