Water → (R)-benzyl 1-cyanoethylcarbamate

HRID 888354Notes

Reaction equation

HRID 888354 reaction equation
[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@H:11]([CH3:15])[C:12]([NH2:14])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1N=C(Cl)N=C(Cl)N=1.O>CN(C)C=O>[CH2:1]([O:8][C:9](=[O:16])[NH:10][C@@H:11]([C:12]#[N:14])[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 7954Cyanuric chlorideHCID 6950969HCID 6950969, compound

Product 1

HCID 10703364(R)-benzyl 1-cyanoethylcarbamateYield 78.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of benzyl[(1R)-2-amino-1-methyl-2-oxoethyl]carbamate (10 g, 45 mmol) in 50 mL of N,N-dimethylformamide was added 2,4,6-trichloro-1,3,5-triazine (4.15 g, 22.5 mmol). After 2 h, 100 mL of water was added and the mixture was filtered. The solids were washed with 100 mL aqueous sodium bicarbonate (2×) and dried under vacuum to give pure benzyl[(1R)-1-cyanoethyl]carbamate (7.2 g). MS 205.2 ((M+1).

Workup

  1. filtrationthe mixture was filtered
  2. washThe solids were washed with 100 mL aqueous sodium bicarbonate (2×)
  3. customdried under vacuum

Sources & evidence

ORD record
ord-37d1811c1ff249a299a8f5c341b43de3
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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