1-Phenethylamine → N-((1R)-1-Phenylethyl)glycine ethyl ester

HRID 393779

反応式

HRID 393779 の反応式
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[CH3:8][CH: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

参加物

5

反応物 3

HCID 74081-PhenethylamineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

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 (DCI/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-874c05c4067740ca9321c982f398fa0b
出典データセット
uspto-grants-2004_10
特許番号
US06809105B2

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