Water → AC1Lgxvo

HRID 2401263Notes

Reaction equation

HRID 2401263 reaction equation
Cl.[NH2:2][C@H:3]([C:7]([NH2:9])=[O:8])[CH:4]([CH3:6])[CH3:5].[C:10](=O)([O-])[OH:11].[Na+].ClC(OC1C=CC([N+]([O-])=O)=CC=1)=O.O>C(#N)C>[CH3:5][CH:4]([C@@H:3]1[NH:2][C:10](=[O:11])[NH:9][C:7]1=[O:8])[CH3:6]

Participants

6

Reactant 4

HCID 962WaterHCID 821294-Nitrophenyl chloroformateHCID 516892Sodium BicarbonateHCID 13689583L-Valinamide--hydrogen chloride (1/1)

Product 1

HCID 853633AC1LgxvoYield 58%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of L-valinamide hydrochloride (1.0 g) and sodium hydrogen carbonate (3.03 g) in acetonitrile (100 mL) was added p-nitrophenyl chloroformate (1.32 g), and the mixture was stirred at room temperature for 3 hr. Water was added thereto, the resulting mixture was stirred at room temperature overnight, and then acetonitrile was distilled off under reduced pressure. After extraction with ethyl acetate, the organic layer was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel cartridge, chloroform/methanol) to afford (5S)-5-(propan-2-yl)imidazolidine-2,4-dione (540 mg).

Workup

  1. stirringthe resulting mixture was stirred at room temperature overnight
  2. distillationacetonitrile was distilled off under reduced pressure
  3. extractionAfter extraction with ethyl acetate
  4. concentrationthe organic layer was concentrated under reduced pressure
  5. customThe residue was purified by column chromatography (silica gel cartridge, chloroform/methanol)

Sources & evidence

ORD record
ord-132f745f687b4f7aba5188080f1dee15
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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