Hydrochloric Acid → S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteine

HRID 486877

Reaction equation

HRID 486877 reaction equation
[CH2:1]([S:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15]([S:22][CH2:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>[OH-].[Na+].CCOCC>[CH2:1]([S:8][CH2:9][C@@H:10]([C:12]([OH:14])=[O:13])[NH:11][C:25](=[O:26])[C:24]([CH3:28])([CH3:29])[CH2:23][S:22][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 193613S-benzyl-L-cysteineHCID 149699863-Benzylthio-2,2-dimethylpropionyl chloride

Product 1

HCID 14969990S-benzyl-N-(3-benzylthio-2,2-dimethylpropionyl)-L-cysteineYield 85.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of S-benzyl-L-cysteine(11.5 g) in 2N sodium hydroxide solution(68 ml), 3-benzylthio-2,2-dimethylpropionyl chloride (14.6 g) dissolved in ether(10 ml) was added dropwise under ice-cooling. After the addition, the reaction mixture was stirred for 20 minutes under ice-cooling and 2 hours at room temperature. The reaction mixture 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 to give 19.4 g(85.1%) of the titled compound.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. additionAfter the addition
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-794df2e6979d43a08be0468fd21596f8
Source dataset
uspto-grants-1994_03
Patent number
US05292926

Linked notes

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