1-Aminocyclohexanecarboxylic acid → 1-[(2-Oxo-2H-pyran-5-carbonyl)amino]cyclohexane-1-carboxylic acid

HRID 1851812Notes

Reaction equation

HRID 1851812 reaction equation
[NH2:1][C:2]1([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[CH2:11](N(CC)CC)C.[C:18]([O:21][CH2:22][CH3:23])(=[O:20])[CH3:19].CN(C)[CH:26]=[O:27]>>[O:20]=[C:18]1[CH:19]=[CH:11][C:23]([C:26]([NH:1][C:2]2([C:8]([OH:10])=[O:9])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]2)=[O:27])=[CH:22][O:21]1

Participants

5

Reactant 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 6228DimethylformamideHCID 8471TriethylamineHCID 8857Ethyl Acetate

Product 1

HCID 246974151-[(2-Oxo-2H-pyran-5-carbonyl)amino]cyclohexane-1-carboxylic acidYield 60%

Procedure

A solution of 2.37 g (10 mmol) of 5-coumarincarboxylic acid N-hydroxysuccinimide ester, 1.43 g (10 mmol) of 1-aminocyclohexanecarboxylic acid and 3.04 g (30 mmol) of triethylamine in 20 ml of dimethylformamide was stirred overnight. Ethyl acetate was added to the reaction solution, and the mixture was washed with a 10% aqueous potassium hydrogensulfate solution and then saturated brine. After it was dried with anhydrous sodium sulfate, the solvent was distilled off under reduced pressure to obtain 1.42 g (60%) of the title compound.

Workup

  1. washthe mixture was washed with a 10% aqueous potassium hydrogensulfate solution
  2. dry with materialAfter it was dried with anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-53906081ac834abdb00630f0e560c419
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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