Methyl cyanoacetate → HCID 178501406, compound

HRID 1815605Notes

Reaction equation

HRID 1815605 reaction equation
Cl.Cl.[CH3:3][O:4][C:5](=[O:14])[C@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[NH2:7].C[O-].[Na+].[Na].[C:19]([CH2:21][C:22](OC)=[O:23])#[N:20]>CO>[C:19]([CH2:21][C:22]([NH:7][C@@H:6]([CH2:8][C:9]1[N:13]=[CH:12][NH:11][CH:10]=1)[C:5]([O:4][CH3:3])=[O:14])=[O:23])#[N:20]

Participants

6

Reactant 4

HCID 7747Methyl cyanoacetateHCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 178419105HCID 178419105, compound

Product 1

HCID 178501406HCID 178501406, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5.0 g (20.4 mmol) of L-histidine methyl ester dihydrochloride were added at room temperature to a sodium methoxide solution obtained by dissolving 0.94 g (40.7 mmol; 1.95 equivalents) of sodium in 100 ml of methanol. After 30 min, 3.03 g (30.6 mmol) of methyl cyanoacetate were added and the mixture was refluxed for 16 h. After cooling to room temperature, the mixture was filtered. The yellowish filtrate was concentrated under reduced pressure and the residue was purified by means of flash chromatography on silica gel (eluent: ethyl acetate→ethyl acetate/methanol 3:1 gradient).

Workup

  1. customobtained
  2. temperaturethe mixture was refluxed for 16 h
  3. filtrationthe mixture was filtered
  4. concentrationThe yellowish filtrate was concentrated under reduced pressure
  5. customthe residue was purified by means of flash chromatography on silica gel (eluent: ethyl acetate→ethyl acetate/methanol 3:1 gradient)

Sources & evidence

ORD record
ord-fff3e77f4b7a4d3d9ab30fe5b75469e3
Source dataset
uspto-grants-2005_04
Patent number
US06878829B2

Reaction notes

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