Diketene → HCID 53467997, compound

HRID 1055246Notes

Reaction equation

HRID 1055246 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH2:8]=[C:9]1[O:13][C:11](=[O:12])[CH2:10]1.C([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1>[O:13]=[C:9]([CH3:8])[CH2:10][C:11]([NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])=[O:12]

Participants

5

Reactant 3

HCID 12661DiketeneHCID 122755Glycine methyl ester hydrochlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 53467997HCID 53467997, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

29.87 g (0.24 mol) of glycine methyl ester hydrochloride were added to a solution of 20.00 g (0.24 mol) of diketene in 250 ml toluene at 0° C. Then, 40.00 g (0.48 mol) NaHCO3 were added and the reaction mixture was stirred overnight at room temperature. Since thin-layer chromatography detected no more starting material, the reaction mixture was filtered, evaporated and the residue purified by column chromatography. This gave 33.4 g (0.19 mol, 81% yield) oil.

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated
  3. customthe residue purified by column chromatography

Sources & evidence

ORD record
ord-e1f8855d8c874a119dd58e061906a6d3
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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