N-Acetyl-L-Cysteine → L-Cysteine, N-acetyl-S-(2-nitrophenyl)-

HRID 1632767Notes

Reaction equation

HRID 1632767 reaction equation
[C:1]([NH:4][C@H:5]([C:8]([OH:10])=[O:9])[CH2:6][SH:7])(=[O:3])[CH3:2].C(=O)(O)[O-].[Na+].F[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N+:23]([O-:25])=[O:24]>O.C(O)C>[N+:23]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=1[S:7][CH2:6][C@@H:5]([C:8]([OH:10])=[O:9])[NH:4][C:1](=[O:3])[CH3:2])([O-:25])=[O:24]

Participants

6

Reactant 3

HCID 12035N-Acetyl-L-CysteineHCID 738951-Fluoro-2-nitrobenzeneHCID 516892Sodium Bicarbonate

Product 1

HCID 185068L-Cysteine, N-acetyl-S-(2-nitrophenyl)-

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 67.8 g of N-acetyl-L-cysteine and 100.8 g of sodium bicarbonate in 300 ml of water is added to 55.4 ml of o-fluoronitrobenzene in 1 l of ethanol. The reaction is heated to reflux for 3 hr with mechanical stirring and allowed to cool to room temperature. After removing the solids by filtration, the solution is concentrated to one fourth of the original volume and diluted with 1 l of water. The aqueous suspension is washed with 200 ml of ether and acidified to pH 1 with 12N aqueous hydrochloric acid. The resulting yellow precipitate is collected by filtration and dried in vacuo at 70° C. over phosphoruos pentoxide to afford S-(o-nitrophenyl)-N-acetyl-L-cysteine; m.p. 175°-176° C.; [α]D =+87.8° (c=1.15, absolute ethanol).

Workup

  1. temperatureThe reaction is heated
  2. temperatureto reflux for 3 hr
  3. customAfter removing the solids
  4. filtrationby filtration
  5. concentrationthe solution is concentrated to one fourth of the original volume
  6. additiondiluted with 1 l of water
  7. washThe aqueous suspension is washed with 200 ml of ether
  8. filtrationThe resulting yellow precipitate is collected by filtration
  9. customdried in vacuo at 70° C. over phosphoruos pentoxide

Sources & evidence

ORD record
ord-4aeb98af8a0543388c132518b8e99136
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

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