1-Aminocyclohexanecarboxylic acid → 1-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acid

HRID 1851796Notes

Reaction equation

HRID 1851796 reaction equation
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[OH-].[Na+].[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18](Cl)=[O:19]>C(OCC)(=O)C>[O:13]1[CH:17]=[CH:16][CH:15]=[C:14]1[C:18]([NH:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1)=[O:19]

Participants

5

Reactant 3

HCID 13661-Aminocyclohexanecarboxylic acidHCID 14798Sodium Hydroxide2×HCID 682422-Furancarbonyl chloride

Product 1

HCID 174552541-[(2-Furanylcarbonyl)amino]cyclohexanecarboxylic acidYield 237.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

71.6 g (0.5 mol) of 1-aminocyclohexanecarboxylic acid was added to 250 ml of an aqueous solution of 20 g (0.5 mol) of sodium hydroxide, and the mixture was stirred at 80° C. for 2 hours. The mixed solution was cooled with ice-water, and 71.8 g (0.2 mol) of 2-furancarbonyl chloride and 100 ml of an aqueous solution of 24 g (0.6 mol) of sodium hydroxide were simultaneously added thereto over approximately 1 hour. The temperature of the reaction solution was slowly returned to room temperature and the solution was stirred overnight. After 80 ml of ethyl acetate was added to the reaction solution and the solution was stirred for 1 hour, the insolubles were removed by filtration. The aqueous layer was separately collected and 49 ml of concentrated hydrochloric acid was added thereto under ice-cooling. The precipitated crystal was collected by filtration and dried under reduced pressure to obtain 112.6 g (95%) of the title compound.

Workup

  1. additionwere simultaneously added
  2. waitover approximately 1 hour
  3. customwas slowly returned to room temperature
  4. stirringthe solution was stirred overnight
  5. stirringthe solution was stirred for 1 hour
  6. customthe insolubles were removed by filtration
  7. customThe aqueous layer was separately collected
  8. addition49 ml of concentrated hydrochloric acid was added
  9. temperatureunder ice-cooling
  10. filtrationThe precipitated crystal was collected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-3653a72ed86a4626918cc2f6e8a7d000
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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