Ethyl bromoacetate → N-((1R)-1-Phenylethyl)glycine ethyl ester

HRID 747917

Reaction equation

HRID 747917 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8]([O-])(=O)[C@@H:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)O.C([N:21](C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[C:11]1([C@H:9]([NH:21][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:8])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 5460269(R)-Mandelate

Product 1

HCID 6455333N-((1R)-1-Phenylethyl)glycine ethyl esterYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Ethyl bromoacetate (4.14 g; 24.8 mmol) was treated with (R) α-methylbenzylamine (3 g, 24.8 mmol) and ethyldiisopropylamine (3.2 g; 24.8 mmol) in toluene (100 mL). After heating at reflux for 18 hours, the mixture was cooled to room temperature and concentrated under reduced pressure. The residue was purified by flash chromatography (SiO2, 20% ethyl acetate/pentane) to provide the title compound (3.2 g, 63% yield). MS (DCl/NH3) m/z 208 (M+H)+.

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 18 hours
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography (SiO2, 20% ethyl acetate/pentane)

Sources & evidence

ORD record
ord-11259bb170614753b0fccd882c74244b
Source dataset
uspto-grants-2008_07
Patent number
US07399765B2

Linked notes

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