Triethylamine → Dimethylaminopropyl thiohydantoin valine

HRID 1647383Notes

Reaction equation

HRID 1647383 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]([CH2:14][CH2:15][CH2:16][N:17]=[C:18]=[S:19])[CH3:13].[CH2:20]([N:22](CC)CC)[CH3:21]>CO>[NH2:6][C@H:5]([C:4]([OH:10])=[O:3])[CH:7]([CH3:9])[CH3:8].[CH3:11][N:12]([CH2:14][CH2:15][CH2:16][N:17]1[CH2:21][C:20](=[O:3])[NH:22][C:18]1=[S:19])[CH3:13]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 87182l-Valine, ethyl esterHCID 1413513-((Dimethylamino)phenyl isothiocyanate

Product 1

HCID 86748773Dimethylaminopropyl thiohydantoin valine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Valine ethyl ester (0.01 mol) in 30 ml of anhydrous methanol was reacted with dimethylaminopropyl isothiocyanate (0.01 mol) for 3 hours at 50° C. The solution was made basic by the addition of two equivalents of triethylamine. Solvent was removed by rotary evaporation. Water was added to the solid residue and the residue was filtered and washed with water. The residue was dissolved in methanol and analyzed by FAB/MS. The expected product, dimethylaminopropyl thiohydantoin valine (MH+=244), was obtained.

Workup

  1. customSolvent was removed by rotary evaporation
  2. additionWater was added to the solid residue
  3. filtrationthe residue was filtered
  4. washwashed with water
  5. dissolutionThe residue was dissolved in methanol

Sources & evidence

ORD record
ord-433c315089c44813a8711837dd95fa0e
Source dataset
uspto-grants-1995_07
Patent number
US05432093

Reaction notes

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