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4-Methyloxybenzyl chloride → S-p-methoxybenzyl-D-cysteine

HRID 744886
Notes
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Reaction equation

HRID 744886 reaction equation
[N+](C1C=CC(COC(N2C[C@@H](S)C[C@H]2C(N2CCN(C(=O)CSC[C@H](C(OCC3C=CC([N+]([O-])=O)=CC=3)=O)NC(OCC3C=CC([N+]([O-])=O)=CC=3)=O)CC2)=O)=O)=CC=1)([O-])=O.Cl.[NH2:62][C@@H:63]([C:66]([OH:68])=[O:67])[CH2:64][SH:65].[CH3:69][O:70][C:71]1[CH:78]=[CH:77][C:74]([CH2:75]Cl)=[CH:73][CH:72]=1>[OH-].[Na+]>[CH3:69][O:70][C:71]1[CH:78]=[CH:77][C:74]([CH2:75][S:65][CH2:64][C@H:63]([C:66]([OH:68])=[O:67])[NH2:62])=[CH:73][CH:72]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 699934-Methyloxybenzyl chlorideHCID 147419D-Cysteine hydrochlorideHCID 56997100(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-(4-(2-((2S)-2-(p-nitrobenzyloxycarbonyl)-2-(p-nitrobenzyloxycarbonylamino) ethylthio)acetyl)piperazine-1-yl)carbonyl-4-mercaptopyrrolidine

Product 1

HCID 7019697S-p-methoxybenzyl-D-cysteine

Reagents, catalysts & solvents 1

HCID 14798
Sodium Hydroxide
Solvent

Procedure

(2S,4S)-1-(p-nitrobenzyloxycarbonyl)-2-(4-(2-((2S)-2-(p-nitrobenzyloxycarbonyl) -2-(p-nitrobenzyloxycarbonylamino) ethylthio)acetyl)piperazine-1-yl)carbonyl-4-mercaptopyrrolidine ##STR13## 1) To 5.05 g of D-cysteine hydrochloride dissolved in 4N sodium hydroxide and cooled on an ice bath was added dropwise 9.39 ml of p-methoxybenzyl chloride, followed by 2 hours of stirring at room temperature. The resulting reaction solution was washed with ether and acidified with concentrated hydrochloric acid, and a crystal was collected by filtration to yield 7.78 g of S-p-methoxybenzyl-D-cysteine in the form of pale yellow crystals.

Workup

  1. temperaturecooled on an ice bath
  2. customThe resulting reaction solution
  3. washwas washed with ether
  4. filtrationa crystal was collected by filtration

Sources & evidence

ORD record
ord-ece2765d9a16442c9fde8aee0ba095e5
Source dataset
uspto-grants-1996_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05559224

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes