Potassium Carbonate → Methyl 4-{[(2-ethoxy-2-oxoethyl)amino]methyl}benzoate

HRID 1650810Notes

Reaction equation

HRID 1650810 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[CH:5][CH:4]=1)=O.Cl.[CH2:14]([O:16][C:17](=[O:20])[CH2:18][NH2:19])[CH3:15].C(=O)([O-])[O-].[K+].[K+].C([BH3-])#N.[Na+]>C(O)C>[CH3:10][O:9][C:7]([C:6]1[CH:11]=[CH:12][C:3]([CH2:1][NH:19][CH2:18][C:17]([O:16][CH2:14][CH3:15])=[O:20])=[CH:4][CH:5]=1)=[O:8]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 15294Methyl 4-FormylbenzoateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5003444Sodium cyanoborohydride

Product 1

HCID 23052534Methyl 4-{[(2-ethoxy-2-oxoethyl)amino]methyl}benzoateYield 50%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To an ethanol solution (50 ml) of methyl 4-formylbenzoate (6.4 g, 40 mmol.) and glycine ethyl ester hydrochloride (5.6 g, 40 mmol.) was added potassium carbonate (5.6 g, 40 mmol.), and the mixture was stirred at room temperature for one hour. To the reaction solution was added sodium cyanoborohydride (2 g, 50 mmol.), and the mixture was stirred for further 18 hours. The reaction solution was subjected to filtration, and the filtrate was concentrated under reduced pressure. To the concentrate was added water (50 ml), and the mixture was subjected to extraction with ethyl acetate. The organic layer was washed with water, dried and concentrated under reduced pressure. The concentrate was purified by means of a silica gel chromatography (developing solvent: IPE:ethyl acetate=1:1) to afford ethyl N-(4-methoxycarbonylbenzyl)aminoacetate (2-g, 5 g, 50%).

Workup

  1. stirringthe mixture was stirred for further 18 hours
  2. filtrationThe reaction solution was subjected to filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. additionTo the concentrate was added water (50 ml)
  5. extractionthe mixture was subjected to extraction with ethyl acetate
  6. washThe organic layer was washed with water
  7. customdried
  8. concentrationconcentrated under reduced pressure
  9. customThe concentrate was purified by means of a silica gel chromatography (developing solvent: IPE:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-64325d599b3d4fbabb570f7fc1062475
Source dataset
uspto-grants-1990_05
Patent number
US04925868

Reaction notes

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