Potassium Carbonate → N(2,2-dimethoxyethyl) glycine tert-butyl ester

HRID 840785Notes

Reaction equation

HRID 840785 reaction equation
[CH3:1][O:2][CH:3]([O:6][CH3:7])[CH2:4][NH2:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]>CN(C=O)C>[C:19]([O:18][C:16](=[O:17])[CH2:15][NH:5][CH2:4][CH:3]([O:6][CH3:7])[O:2][CH3:1])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate2×HCID 89728Aminoacetaldehyde dimethyl acetal

Product 1

HCID 10846528N(2,2-dimethoxyethyl) glycine tert-butyl esterYield 42.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of 2,2-dimethoxyethylamine (15 g, 143 mmol), anhydrous potassium carbonate (20 g, 145 mmol) and DMF (140 mL) was added tert-butyl bromoacetate (11.5 mL, 71.2 mmol). After stirring at room temperature for 2 hours, another portion of tert-butyl bromoacetate (11.5 mL, 71.2 mmol) was added to the mixture, which was stirred overnight at room temperature. To the reaction mixture was added ice-water (140 mL). The mixture was extracted with EtOAc. The organic layer was washed with sat. NaCl, dried over Na2SO4, filtered and evaporated. The residue was subjected to distillation under reduced pressure to give the title compound as a colorless oil (6.61 g).

Workup

  1. stirringwas stirred overnight at room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. washThe organic layer was washed with sat. NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customevaporated
  7. distillationThe residue was subjected to distillation under reduced pressure

Sources & evidence

ORD record
ord-672418aa8499445a993aff29ffdee422
Source dataset
uspto-grants-2002_04
Patent number
US06369063B1

Reaction notes

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