Water → Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

HRID 1459112

Reaction equation

HRID 1459112 reaction equation
[CH2:1]([NH:8][CH2:9][CH2:10][OH:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(=O)([O-])[O-].[K+].[K+].[C:19]([O:23][C:24](=[O:27])[CH2:25]Br)([CH3:22])([CH3:21])[CH3:20]>O1CCCC1>[C:19]([O:23][C:24](=[O:27])[CH2:25][N:8]([CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)[CH2:9][CH2:10][OH:11])([CH3:22])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 962WaterHCID 4348BenzylethanolamineHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetate

Product 1

HCID 15817339Tert-butyl 2-(benzyl (2-hydroxyethyl)amino)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

15.1 g (100 mmol) of N-benzylethanolamine is dissolved in 50 ml of tetrahydrofuran and mixed with 15 ml of water and 13.8 g (100 mmol) of potassium carbonate. After instillation of 20.5 g (105 mmol) of bromoacetic acid-tert-butyl ester, it is stirred for 6 hours at 65° C. After cooling, it is filtered, concentrated by evaporation in a vacuum and the residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine. The product fractions are concentrated by evaporation in a vacuum and dried.

Workup

  1. temperatureAfter cooling
  2. filtrationit is filtered
  3. concentrationconcentrated by evaporation in a vacuum
  4. customthe residue is chromatographed on silica gel with diethyl ether/hexane/triethylamine
  5. concentrationThe product fractions are concentrated by evaporation in a vacuum
  6. customdried

Sources & evidence

ORD record
ord-83a471c539924db8ab003c2bbdffb796
Source dataset
uspto-grants-1998_12
Patent number
US05853699

Linked notes

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