p-Xylyl bromide → S-p-Methylbenzyl-L-cysteine

HRID 1003649Notes

Reaction equation

HRID 1003649 reaction equation
O.Cl.[NH2:3][C@H:4]([C:7]([OH:9])=[O:8])[CH2:5][SH:6].Br[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1>[OH-].[Na+].C(O)C>[CH3:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][S:6][CH2:5][C@@H:4]([C:7]([OH:9])=[O:8])[NH2:3])=[CH:14][CH:13]=1

Participants

5

Reactant 2

HCID 7721p-Xylyl bromideHCID 23462L-Cysteine hydrochloride monohydrate

Product 1

HCID 13994756S-p-Methylbenzyl-L-cysteine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

L-Cysteine hydrochloride monohydrate (2.0 g) is dissolved in a 2 N aqueous sodium hydroxide solution (11.4 ml). To the solution is added a solution of α-bromo-p-xylene (2.3 g) in ethanol (10 ml). The mixture is stirred at room temperature for 40 minutes, and precipitating crystals are filtered off. The obtained crystals are purified by recrystallization to give the titled compound.

Workup

  1. customprecipitating crystals
  2. filtrationare filtered off
  3. customThe obtained crystals are purified by recrystallization

Sources & evidence

ORD record
ord-2bd0214789884754b1d748c3c1b81b2a
Source dataset
uspto-grants-2000_04
Patent number
US06046235

Reaction notes

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