(-)-Cystine → N,N'-Bis[2-methyl-2-(methylthio)propanoyl]-L-cystine

HRID 462655

Reaction equation

HRID 462655 reaction equation
[CH2:1]([S:7][S:8][CH2:9][C@H:10]([NH2:14])[C:11]([OH:13])=[O:12])[C@H:2]([NH2:6])[C:3]([OH:5])=[O:4].[CH3:15][C:16]([S:21][CH3:22])([CH3:20])[C:17](Cl)=[O:18]>[OH-].[Na+]>[CH3:15][C:16]([S:21][CH3:22])([CH3:20])[C:17]([NH:6][C@H:2]([C:3]([OH:5])=[O:4])[CH2:1][S:7][S:8][CH2:9][C@H:10]([NH:14][C:17](=[O:18])[C:16]([S:21][CH3:22])([CH3:20])[CH3:15])[C:11]([OH:13])=[O:12])=[O:18]

Participants

4

Reactant 2

HCID 67678(-)-CystineHCID 134719922-Methyl-2-(methylthio)propanoyl chloride

Product 1

HCID 13471994N,N'-Bis[2-methyl-2-(methylthio)propanoyl]-L-cystineYield 83.6%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of 3.1 g (13 mM) of L-cystine in 105 ml of 0.5 N sodium hydroxide, 4.0 g (26 mM) of 2-methyl-2-(methylthio)propanoyl chloride is added dropwise at 5°-10° C. After the addition the reaction mixture is stirred for 45 minutes at the same temperature and for additional 20 minutes at the room temperature. The reaction mixture is washed with ether, acidified with 6N hydrochloric acid and extracted with ethyl acetate. The organic layer is washed with water and dried. Ehtyl acetate is distillated off and the residue is purified by silica gel column chromatography to give 5.1 g (83%) of the titled compound.

Workup

  1. additionAfter the addition the reaction mixture
  2. washThe reaction mixture is washed with ether
  3. extractionextracted with ethyl acetate
  4. washThe organic layer is washed with water
  5. customdried
  6. customthe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-4c52b1ec942b42118310243abe50d3ae
Source dataset
uspto-grants-1985_05
Patent number
US04517123

Linked notes

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