Water → S-(o-Nitrophenyl)-N-acetyl-D-cysteine

HRID 53118Notes

Reaction equation

HRID 53118 reaction equation
[C:1]([NH:4][C@@H:5]([C:8]([OH:10])=[O:9])[CH2:6][SH:7])(=[O:3])[CH3:2].F[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].C(=O)(O)[O-].[Na+].O>C(O)C>[N+:18]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[S:7][CH2:6][C@H:5]([C:8]([OH:10])=[O:9])[NH:4][C:1](=[O:3])[CH3:2])([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 962WaterHCID 738951-Fluoro-2-nitrobenzeneHCID 94364N-Acetyl-D-cysteineHCID 516892Sodium Bicarbonate

Product 1

HCID 13375098S-(o-Nitrophenyl)-N-acetyl-D-cysteineYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 9.28 g (56.9 mmol) of (S)-N-acetyl-cysteine, 7.43 mL (70.5 mmol) of 1-fluoro-2-nitrobenzene and 13.66 g (163 mmol) of sodium bicarbonate was refluxed in 136 mL of ethanol and 41 mL of water for 3 hours. The mixture was cooled to room temperature and the solvent evaporated. The residue was dissolved in 136 mL of water and extracted with ether. The water solution was then acidified to pH=1with 12N hydrochloric acid (HCl). The resulting yellow precipitate was filtered to yield 13.6 g (84%) of product.

Workup

  1. customthe solvent evaporated
  2. dissolutionThe residue was dissolved in 136 mL of water
  3. extractionextracted with ether
  4. filtrationThe resulting yellow precipitate was filtered

Sources & evidence

ORD record
ord-c777ee5d38104e338cdf0476fa8d453a
Source dataset
uspto-grants-1997_04
Patent number
US05618808

Reaction notes

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