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

HRID 1642159

반응식

HRID 1642159 반응식
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

참가 물질

5

반응물 3

HCID 74081-PhenethylamineHCID 7748Ethyl bromoacetateHCID 81531Diisopropylethylamine

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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)+.

후처리

  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)

출처 및 근거

ORD 기록
ord-5eedbaa1ab04496a94960ab181062da5
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119635B2

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