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

HRID 1627438Notes

Reaction equation

HRID 1627438 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 20 g (0.5 mol) of sodium hydroxide in 250 ml of aqueous solution, and the mixture was stirred at 80° C. for 2 hours. The mixture solution was cooled by ice-water, 71.8 g (0.2 mol) of 2-furancarbonyl chloride and 24 g (0.6 mol) of sodium hydroxide in 100 ml of aqueous solution were simultaneously added thereto over approximately 1 hour. The reaction solution was slowly returned to room temperature and stirred overnight. 80 ml of ethyl acetate was added to the reaction solution and after the mixture 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. stirringstirred overnight
  5. stirringafter the mixture 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-7d44dea7f7484073b7b439aa498f12c4
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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