Dimethylthiocarbamoyl chloride → Dimethylthiocarbamoyl valine

HRID 260133

Reaction equation

HRID 260133 reaction equation
C([O:3][C:4](=[O:10])[C@H:5]([CH:7]([CH3:9])[CH3:8])[NH2:6])C.[CH3:11][N:12]([CH3:16])[C:13](Cl)=[S:14]>C(#N)C>[CH3:11][N:12]([CH3:16])[C:13]([NH:6][C@H:5]([C:4]([OH:3])=[O:10])[CH:7]([CH3:9])[CH3:8])=[S:14]

Participants

4

Reactant 2

HCID 27871Dimethylthiocarbamoyl chlorideHCID 87182l-Valine, ethyl ester

Product 1

HCID 53885838Dimethylthiocarbamoyl valine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Valine ethyl ester (0.0028 mol) in 10 ml acetonitrile was reacted with dimethylthiocarbamoyl chloride (0.0056 mol) at 50° C. for 2 hours. Solvent acetonitrile was removed by rotary evaporation. Trifluoroacetic acid (10 ml) was added and the mixture stirred at room temperature for 15 min. The trifluoroacetic acid was removed by rotary evaporation. The residue was dissolved in water and analyzed by FAB/MS. The expected product, dimethylthiocarbamoyl valine (MH+=205), was obtained.

Workup

  1. customSolvent acetonitrile was removed by rotary evaporation
  2. additionTrifluoroacetic acid (10 ml) was added
  3. customThe trifluoroacetic acid was removed by rotary evaporation
  4. dissolutionThe residue was dissolved in water

Sources & evidence

ORD record
ord-7c3f4ac9582a492d88c902c8d1fa939d
Source dataset
uspto-grants-1996_06
Patent number
US05525707

Linked notes

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