Water → (R)-benzyl 1-cyanoethylcarbamate

HRID 1909112Notes

Reaction equation

HRID 1909112 reaction equation
[NH2:1][C:2](=O)[C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[CH3:4].ClC1N=C(Cl)N=C(Cl)N=1.O>CN(C)C=O>[C:2]([C@H:3]([NH:5][C:6](=[O:15])[O:7][CH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1)[CH3:4])#[N: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-b98e1b25f55f41b8a66792fecb5040f4
Source dataset
uspto-grants-2013_12
Patent number
US08598209B2

Reaction notes

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