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

HRID 73851Notes

Reaction equation

HRID 73851 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. Under reduced pressure the reaction mixture was distilled off, 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. temperatureheated
  2. temperatureunder reflux overnight
  3. distillationUnder reduced pressure the reaction mixture was distilled off
  4. additionethyl acetate was 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-517c71ad786d458685c3b1fe33258f6b
Source dataset
uspto-grants-2014_09
Patent number
US08829209B2

Reaction notes

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