Sodium Methoxide → N-(5-Methoxy-2-nitrophenyl)-S-methyl-L-cysteine

HRID 877

Reaction equation

HRID 877 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][S:11][CH3:12])[CH:7]=1.[CH3:19][O-:20].[Na+]>CO>[CH3:19][O:20][C:2]1[CH:3]=[CH:4][C:5]([N+:16]([O-:18])=[O:17])=[C:6]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH2:10][S:11][CH3:12])[CH:7]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57293179N-(5-Fluoro-2-nitrophenyl)-S-methyl-L-cysteine

Product 1

HCID 57147352N-(5-Methoxy-2-nitrophenyl)-S-methyl-L-cysteine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

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.

Workup

  1. temperaturewhile cooling by means of an ice bath
  2. temperatureThe mixture is then heated
  3. temperatureto reflux for 2 hours
  4. stirringwhile stirring

Sources & evidence

ORD record
ord-49f2d19dd08c44a6a1032e78dc4359e1
Source dataset
uspto-grants-1998_03
Patent number
US05723461

Linked notes

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