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

HRID 1851831Notes

Reaction equation

HRID 1851831 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 refluxed under heating 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 the residue was purified by silica gel chromatography to obtain 384 mg (12.5%) of the title compound.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating 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
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-429bbaea4d8b40b8af87403e482879a2
Source dataset
uspto-grants-2015_02
Patent number
US08957205B2

Reaction notes

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