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

HRID 747917

反応式

HRID 747917 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-11259bb170614753b0fccd882c74244b
出典データセット
uspto-grants-2008_07
特許番号
US07399765B2

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