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

HRID 1627454Notes

Reaction equation

HRID 1627454 reaction equation
[O:1]1[C:11]2C=CC=[C:7](C(O)=O)[C:6]=2[CH:5]=[CH:4][C:2]1=[O:3].[NH2:15][C:16]1([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.C(N(CC)CC)C.C(OCC)(=[O:34])C>CN(C)C=O>[O:3]=[C:2]1[CH:4]=[CH:5][C:6]([C:7]([NH:15][C:16]2([C:22]([OH:24])=[O:23])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[O:34])=[CH:11][O:1]1

Participants

6

Reactant 4

HCID 13661-Aminocyclohexanecarboxylic acidHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 71736442HCID 71736442, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.37 g (10 mmol) of 5-coumarincarboxylic acid N-hydroxysuccineimide ester and a solution of 1.43 g (10 mmol) of 1-aminocyclohexanecarboxylic acid and 3.04 g (30 mmol) of triethylamine in 20 ml of dimethylformamide were 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-af6b91d02d9046488a430ec046b58bfc
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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