Benzyl isocyanate → HCID 64699649, compound

HRID 2361946Notes

Reaction equation

HRID 2361946 reaction equation
[NH2:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5].[CH2:9]([N:16]=[C:17]=[O:18])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>C1COCC1.C(OCC)(=O)C>[CH2:9]([NH:16][C:17](=[O:18])[NH:1][C:2]([CH3:8])([CH3:7])[CH2:3][C:4]([OH:6])=[O:5])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 2

HCID 76639Benzyl isocyanateHCID 27609333-Amino-3-methylbutanoic acid

Product 1

HCID 64699649HCID 64699649, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-amino-3-methylbutanoic acid (5.86 g, 34.2 mmol) in THF was added benzyl isocyanate (5.87 ml, 47.5 mmol) and the mixture was stirred at room temperature overnight. The reaction mixture was diluted with ethyl acetate (100 ml) and washed with water (100 ml) and brine (100 ml). Then the organic layer was dried over magnesium sulfate and filtered. The filtrate was concentrated in vacuo. The crude residue was subjected to silica gel column chromatography (eluent: chloroform:methanol=95:5) to obtain the title compound (5.73 g, 67%).

Workup

  1. washwashed with water (100 ml) and brine (100 ml)
  2. dry with materialThen the organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-af6427f2f62c4ecd88182c6c165c50d4
Source dataset
uspto-grants-2014_04
Patent number
US08691819B2

Reaction notes

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