L-Valine → N-[[1-[(2-furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valine

HRID 1627472Notes

Reaction equation

HRID 1627472 reaction equation
[NH2:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4].[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]1[O:18][C:17](=[O:19])[C:16]2([CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[N:15]=1>CN1CCOCC1>[O:9]1[CH:13]=[CH:12][CH:11]=[C:10]1[C:14]([NH:15][C:16]1([C:17]([NH:1][C@H:2]([C:6]([OH:8])=[O:7])[CH:3]([CH3:5])[CH3:4])=[O:19])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[O:18]

Participants

4

Reactant 2

HCID 6287L-ValineHCID 247399602-(2-Furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one

Product 1

HCID 24737720N-[[1-[(2-furanylcarbonyl)amino]cyclohexyl]carbonyl]-L-valineYield 12.5%

Reagents, catalysts & solvents 1

HCID 79724-MethylmorpholineSolvent

Procedure

10 ml of N-methylmorpholine was added to 1.0 g (9.1 mmol) of L-valine and 2.0 g (9.1 mmol) of 2-(2-furanyl)-3-oxa-1-azaspiro[4.5]dec-1-en-4-one, and the mixture was stirred and heated under reflux overnight. The reaction solution was distilled off under reduced pressure, ethyl acetate was added thereto, and the mixture was washed with a 10% aqueous potassium hydrogensulfate solution and then saturated brine, followed by drying with anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and it was purified by silica gel chromatography to obtain 384 mg (12.5%) of the title compound.

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. distillationThe reaction solution was distilled off under reduced pressure, ethyl acetate
  4. additionwas added
  5. washthe mixture was washed with a 10% aqueous potassium hydrogensulfate solution
  6. dry with materialby drying with anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure and it
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-017cd517dc2e43be899edeef9286c1c5
Source dataset
uspto-grants-2014_07
Patent number
US08785631B2

Reaction notes

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