Reaction #973

ord-49f2d19dd08c44a6a1032e78dc4359e1

Reaction equation

CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O
N-(5-fluoro-2-nitrophenyl)-S-methyl-L-cysteine
CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O
N-(5-Fluoro-2-nitrophenyl)-S-methyl-L-cysteine
C[O-].[Na+]
sodium methoxide
→
COc1ccc([N+](=O)[O-])c(N[C@@H](CSC)C(=O)O)c1
N-(5-Methoxy-2-nitrophenyl)-S-methyl-L-cysteine

Reactants

CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O
N-(5-fluoro-2-nitrophenyl)-S-methyl-L-cysteine
CSC[C@H](Nc1cc(F)ccc1[N+](=O)[O-])C(=O)O
N-(5-Fluoro-2-nitrophenyl)-S-methyl-L-cysteine
C[O-].[Na+]
sodium methoxide

Reagents

None

Solvents

CO
methanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Temperaturewhile cooling by means of an ice bath
  2. 2
    TemperatureThe mixture is then heated
  3. 3
    Temperatureto reflux for 2 hours
  4. 4
    workup.STIRRINGwhile stirring

Procedure

27 g of N-(5-fluoro-2-nitrophenyl)-S-methyl-L-cysteine (0.1 mol) from Example 1 are dissolved in 150 ml of absolute methanol in a four-necked flask, and 14.4 g of 95% sodium methoxide (0.25 mmol) are added in portions, within the space of 20 minutes and under argon, to this solution while stirring well and while cooling by means of an ice bath. The mixture is then heated to reflux for 2 hours while stirring. TLC monitoring then indicates that the reaction is complete.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05723461uspto-grants-1998_03