Reacción #973

ord-49f2d19dd08c44a6a1032e78dc4359e1

Ecuación de reacción

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

Reactantes

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

Reactivos

Ninguno

Disolventes

CO
methanol

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Temperaturawhile cooling by means of an ice bath
  2. 2
    TemperaturaThe mixture is then heated
  3. 3
    Temperaturato reflux for 2 hours
  4. 4
    workup.STIRRINGwhile stirring

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05723461uspto-grants-1998_03