Potassium Cyanide → N-(p-chlorophenyl)valine

HRID 648291Notes

Reaction equation

HRID 648291 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH:12]([CH:13]([CH3:15])[CH3:14])[C:11](=[O:16])[O:10]C2=O)=[CH:4][CH:3]=1.[C-]#N.[K+]>C1C=CC=CC=1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.CCOCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C@H:12]([C:11]([OH:16])=[O:10])[CH:13]([CH3:15])[CH3:14])=[CH:6][CH:7]=1

Participants

6

Reactant 2

HCID 9032Potassium CyanideHCID 132294943-(4-Chlorophenyl)-4-isopropyloxazolidine-2,5-dione

Product 1

HCID 13796078N-(p-chlorophenyl)valine

Reagents, catalysts & solvents 3

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of m-naphthoxybenzaldehyde (0.43 g), 3-(4-chlorophenyl)-4-isopropyloxazolidine-2,5-dione (0.5 g), and potassium cyanide (0.23 g) in benzene (about 10 ml), with stirring, is added benzyl triethyl ammonium chloride (about 0.1 g). The reaction mixture is stirred for about 50 hr. The reaction is then worked up by taking up in ether, washing with water and brine, drying over sodium sulfate and evaporating. The concentrate is plated, prep. TLC, eluting with 20% ether/hexane to yield the m-naphthoxy-α-cyanobenzyl ester of N-(4-chlorophenyl)valine, MS m/e 484 (M+).

Workup

  1. stirringThe reaction mixture is stirred for about 50 hr
  2. washwashing with water and brine
  3. dry with materialdrying over sodium sulfate
  4. customevaporating
  5. washTLC, eluting with 20% ether/hexane

Sources & evidence

ORD record
ord-3cf3192f2cea40b5a5601f2881eb0463
Source dataset
uspto-grants-1983_10
Patent number
US04411912

Reaction notes

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