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

HRID 542369Notes

Reaction equation

HRID 542369 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 containing 3.43 g of sodium hydrogen sulfite in 20 ml of water was added to 2.81 g of N-carbobenzoxy-L-leucinal, and the mixture was stirred for 14 hours under ice-cooling. A solution of 1.41 g of potassium cyanide in 50 ml of water and 200 ml of ethyl acetate were added to the reaction mixture, and the mixture was stirred for 4 hours at room temperature. The ethyl acetate layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate, and evaporated under reduced pressure to give 2.54 g of 3-carbobenzoxyamino-2-hydroxy-5-methylhexanenitrile as a colorless oil. A mixture of 20 ml of dioxane and 20 ml of concentrated hydrochloric acid was added to 500 mg of the nitrile, and the mixture was heated under reflux for 12 hours. The reaction mixture was evaporated under reduced pressure, and the residual crystals were purified by cation exchange column chromatography (eluent: a 2N aqueous NH4OH solution) to obtain 254 mg of (2RS, 3S)-3-amino-2-hydroxy-5-methylhexanoic acid as colorless crystals (a mixture in ratio of 2R and 2S being about 7:3).

Workup

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

Sources & evidence

ORD record
ord-10bdeaef093e438ba02f9c917b8d6dbb
Source dataset
uspto-grants-1987_04
Patent number
US04656269

Reaction notes

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