Acetic Acid → HCID 15170719, compound

HRID 486883

Reaction equation

HRID 486883 reaction equation
[SH:1][C:2]([CH3:13])([CH3:12])[C:3]([NH:5][C@H:6]([C:9]([OH:11])=[O:10])[CH2:7][SH:8])=[O:4].[C:14](O)(=O)C>CCOCC.[N+](=C)=[N-]>[CH3:14][O:10][C:9](=[O:11])[C@H:6]([CH2:7][SH:8])[NH:5][C:3](=[O:4])[C:2]([SH:1])([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 656604Bucillamine

Product 1

HCID 15170719HCID 15170719, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 9550DiazomethaneSolvent

Procedure

To a solution of N-(2-mercapto-2-methylpropionyl)-L-cysteine (1.0 g) in ether(3 ml), diazomethane dissolved in ether(12 ml) was added dropwise under ice-cooling. After the addition, acetic acid was added to the reaction mixture. The reaction mixture was washed with saturated sodium hydrogen carbonate solution and 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 1.0 g(94%) of the titled compound.

Workup

  1. additionwas added dropwise under ice-
  2. temperaturecooling
  3. additionwas added to the reaction mixture
  4. washThe reaction mixture was washed with saturated sodium hydrogen carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-d22ad1ba57f24a5b9ffc12e56b23c69d
Source dataset
uspto-grants-1994_03
Patent number
US05292926

Linked notes

Loading…