Carbobenzoxyglycylglycine → (2-(((Benzyloxy)carbonyl)amino)acetamido)methyl acetate

HRID 1389483Notes

Reaction equation

HRID 1389483 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]([NH:15][CH2:16]C(O)=O)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O-:23])(=[O:22])[CH3:21].[Na+]>C(O)(=O)C.[Pt]>[C:20]([O:23][CH2:16][NH:15][C:13](=[O:14])[CH2:12][NH:11][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 95686CarbobenzoxyglycylglycineHCID 517045Sodium Acetate

Product 1

HCID 20473730(2-(((Benzyloxy)carbonyl)amino)acetamido)methyl acetateYield 60%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 176Acetic AcidSolvent

Procedure

Benzyloxycarbonylglycylglycine (3.99 g, 15 mmole) was suspended in a solution of anhydrous sodium acetate (0.9 g, 11 mmole) in glacial acetic acid (75 ml). The mixture was stirred and ice-cooled while being electrolysed (two 5 sq. cm. platinum foil electrodes placed 2 mm apart) using a current of 200-250 mA for 5 hours. The acetic acid was evaporated under reduced pressure and the residue was dissolved in ethyl acetate (150 ml). The solution was washed with saturated sodium bicarbonate solution (5) ml portions, until the wash remained alkaline) and then with water (50 ml). The solution was dried (magnesium sulphate) and the solvent was evaporated under reduced pressure to yield the title compound as colorless crystals (1.85 g, 6.6 mmole).

Workup

  1. temperatureice-cooled
  2. customfor 5 hours
  3. customThe acetic acid was evaporated under reduced pressure
  4. dissolutionthe residue was dissolved in ethyl acetate (150 ml)
  5. washThe solution was washed with saturated sodium bicarbonate solution (5) ml portions, until the wash
  6. dry with materialThe solution was dried (magnesium sulphate)
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-e085e3655fab43848d81fc3bb58519f2
Source dataset
uspto-grants-1981_01
Patent number
US04244965

Reaction notes

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