Ammonium Hydroxide → S-o-nitrophenyl-L-cysteine

HRID 1632768Notes

Reaction equation

HRID 1632768 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@@H:12]([C:17]([OH:19])=[O:18])[NH:13]C(=O)C)([O-:3])=[O:2].[OH-].[NH4+]>S(=O)(=O)(O)O.O>[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[S:10][CH2:11][C@@H:12]([C:17]([OH:19])=[O:18])[NH2:13])([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 14923Ammonium HydroxideHCID 185068L-Cysteine, N-acetyl-S-(2-nitrophenyl)-

Product 1

HCID 124713S-o-nitrophenyl-L-cysteine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1118Sulfuric AcidSolvent

Procedure

A solution of 71 g of S-(o-nitrophenyl)-N-acetyl-L-cysteine in 300 ml of 18M sulfuric acid and 1200 ml of water is heated to reflux for 30 min. The solution is cooled in ice and treated with 700 ml of concentrated ammonium hydroxide. The resulting solid is recrystallized from boiling water to afford S-(o-nitrophenyl)-L-cysteine; m.p. 168°-171° C.; [α]D =+67.3° (c=1.1, 1N hydrochloric acid).

Workup

  1. temperatureto reflux for 30 min
  2. temperatureThe solution is cooled in ice
  3. customThe resulting solid is recrystallized

Sources & evidence

ORD record
ord-aec0a29497ac4592b79b9a5c838332be
Source dataset
uspto-grants-1984_10
Patent number
US04477464

Reaction notes

Loading…