Potassium Cyanide → 3-Carbobenzoxyamino-2-hydroxy-5-methylhexanenitrile

HRID 1722895Notes

Reaction equation

HRID 1722895 reaction equation
S(=O)(O)[O-].[Na+].[C:6]([NH:16][C@H:17]([CH:22]=[O:23])[CH2:18][CH:19]([CH3:21])[CH3:20])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[C-:24]#[N:25].[K+]>O.C(OCC)(=O)C>[C:6]([NH:16][CH:17]([CH2:18][CH:19]([CH3:20])[CH3:21])[CH:22]([OH:23])[C:24]#[N:25])([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Participants

6

Reactant 3

HCID 9032Potassium CyanideHCID 10911911N-carbobenzoxy-L-leucinalHCID 23665763Sodium Bisulfite

Product 1

HCID 138486293-Carbobenzoxyamino-2-hydroxy-5-methylhexanenitrileYield 81.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.43 g of sodium bisulfite in 20 ml of water was added to 2.81 g of N-carbobenzoxy-L-leucinal, and the mixture was stirred under ice-cooling for 14 hours. To the reaction mixture were added a solution of 1.41 g of potassium cyanide in 50 ml of water and 200 ml of ethyl acetate, and the mixture was stirred at room temperature for 4 hours. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over magnesium sulfate, and concentrated under reduced pressure to obtain 2.54 g of 3-carbobenzoxyamino-2-hydroxy-5-methylhexanenitrile as a colorless oil.

Workup

  1. temperaturecooling for 14 hours
  2. stirringthe mixture was stirred at room temperature for 4 hours
  3. washThe ethyl acetate layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ee593498200d4266a9b6d9e461d60221
Source dataset
uspto-grants-1989_08
Patent number
US04857650

Reaction notes

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