Ethyl bromoacetate → HCID 86663849, compound

HRID 1022572Notes

Reaction equation

HRID 1022572 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][OH:17])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21].[H-].[Na+]>C1COCC1>[C:1]([O:5][C:6]([N:8]([CH2:15][CH2:16][O:17][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[O:7])([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 44614461HCID 44614461, compound

Product 1

HCID 86663849HCID 86663849, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl N-(tert-butoxycarbonyl)-N-(2-hydroxyethyl)glycinate (1.2 g) in THF (17 mL) was added ethyl bromoacetate (0.8 ml) under ice-cooling, and the mixture was stirred for 5 min. To this solution was added sodium hydride (288 mg), and the mixture was stirred under ice-cooling for 5 min, and at room temperature for 60 min. The reaction mixture was ice-cooled again, ice water was added, and the mixture was extracted with ethyl acetate. The extract was washed successively with water and brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (788 mg).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 5 min
  4. waitat room temperature for 60 min
  5. temperaturecooled again
  6. extractionthe mixture was extracted with ethyl acetate
  7. washThe extract was washed successively with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. customThe solvent was evaporated under reduced pressure
  10. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-54a8d72f979d4be390dd360a44754608
Source dataset
uspto-grants-2014_05
Patent number
US08722662B2

Reaction notes

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