4-Methyloxybenzyl chloride → HCID 15170715, compound

HRID 486880

Reaction equation

HRID 486880 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].[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Cl)=[CH:18][CH:17]=1>C(O)C.[OH-].[Na+]>[CH3:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][S:8][CH2:7][C@@H:6]([C:9]([OH:11])=[O:10])[NH:5][C:3](=[O:4])[C:2]([S:1][CH2:20][C:19]2[CH:22]=[CH:23][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)([CH3:13])[CH3:12])=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 699934-Methyloxybenzyl chlorideHCID 656604Bucillamine

Product 1

HCID 15170715HCID 15170715, compoundYield 67%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a stirred solution of N-(2-mercapto-2-methylpropionyl)-L-cysteine (2.0 g) in ethanol(10 ml), 4N sodium hydroxide solution(7.7 ml) and paramethoxybenzyl chloride(3.0 ml) were added dropwise under ice-cooling and under nitrogen atomosphere. After the addition, the reaction mixture was stirred for 2 hours under ice-cooling and 2 hours at room temperature. The reaction mixture was concentrated in vacuo, acidified with 2N hydrochloric acid and extracted with ether. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo to give crystals. The crystals were recrystallized with ether to give 2.8 g(67%) of the titled compound.

Workup

  1. temperaturecooling and under nitrogen atomosphere
  2. additionAfter the addition
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. extractionextracted with ether
  5. washThe organic layer was washed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo
  8. customto give crystals
  9. customThe crystals were recrystallized with ether

Sources & evidence

ORD record
ord-8fb0a75d47eb4fcebc445aca55739003
Source dataset
uspto-grants-1994_03
Patent number
US05292926

Linked notes

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