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

HRID 2251420Notes

Reaction equation

HRID 2251420 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][C@@H:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(C(C)C)C(C)C)C>C1(C)C=CC=CC=1>[C:10]1([C@H:9]([NH:16][CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])[CH3:8])[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 6431891-Phenethylamine, (+)-

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 (DCI/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-ea835f075e8642f397adc69f8d5a52c1
Source dataset
uspto-grants-2008_01
Patent number
US07319106B2

Reaction notes

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