Ammonium Chloride → N-(2,2-dimethyl-3-mercaptopropionyl)-L-cysteine

HRID 486878Notes

Reaction equation

HRID 486878 reaction equation
C([S:8][CH2:9][C@@H:10]([C:26]([OH:28])=[O:27])[NH:11][C:12](=[O:25])[C:13]([CH3:24])([CH3:23])[CH2:14][S:15]CC1C=CC=CC=1)C1C=CC=CC=1.[Na].[Cl-].[NH4+]>N>[CH3:23][C:13]([CH3:24])([CH2:14][SH:15])[C:12]([NH:11][C@H:10]([C:26]([OH:28])=[O:27])[CH2:9][SH:8])=[O:25]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 5360545SodiumHCID 14969990S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine

Product 1

HCID 9859532N-(2,2-dimethyl-3-mercaptopropionyl)-L-cysteineYield 69.6%

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

To a solution of S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine (18.0 g) in liquid ammonia(250 ml), metallic sodium (5.0 g) cut into small pieces was added. To this solution, ammonium chloride was added and then liquid ammonia was evaporated. To the residue, water was added, and the solution was washed with ethyl acetate. The aqueous layer was acidified with 6N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography and recrystallized with a mixture of ethyl acetate and cyclohexane to give 7.1 g(69.6%) of the titled compound. The physical data were identical with those of the compound obtained in Example 2.

Workup

  1. additionwas added
  2. customliquid ammonia was evaporated
  3. additionTo the residue, water was added
  4. washthe solution was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe oily residue was purified by a silica gel column chromatography
  10. customrecrystallized with a mixture of ethyl acetate and cyclohexane

Sources & evidence

ORD record
ord-93789ff0e644444583f49f8ffa0ad82e
Source dataset
uspto-grants-1994_03
Patent number
US05292926

Reaction notes

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