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Hydrochloric Acid → Diethyl acetamido(3-phenylpropyl)propanedioate

HRID 862808
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HRID 862808 반응식
[C:1]([NH:4][CH:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2].[C:16]1([CH2:22][CH2:23][CH2:24]Br)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.Cl>C(O)C>[C:1]([NH:4][C:5]([CH2:24][CH2:23][CH2:22][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]([O:8][CH2:9][CH3:10])=[O:7])(=[O:3])[CH3:2]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 313Hydrochloric AcidHCID 12503(3-Bromopropyl)benzeneHCID 14041Acetamidomalonic acid diethyl ester

생성물 1

HCID 21849514Diethyl acetamido(3-phenylpropyl)propanedioate

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
50 °C

실험 절차

Sodium (0.23 g) was added to 15 ml of absolute ethanol and the mixture was stirred at room temperature for 30 minutes in a nitrogen flow to give a 10 mmol solution of sodium ethoxide in ethanol. To this solution, 1.98 g of diethyl 2-acetamidomalonate was added and the mixture was heated at 50° C. for 30 minutes in a stream of nitrogen. 3-Phenylpropyl bromide was added thereto at room temperature and the mixture was refluxed under heating for 24 hours. The mixture was neutralized with dilute hydrochloric acid and ethanol was distilled away. The resultant residue was extracted with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was distilled away and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-1:1) and recrystallized from diisopropyl ether-hexane to give 800 mg of diethyl 2-acetamido-2-(3-phenylpropyl)malonate as white crystals.

후처리

  1. temperatureat room temperature and the mixture was refluxed
  2. temperatureunder heating for 24 hours
  3. distillationwas distilled away
  4. extractionThe resultant residue was extracted with ethyl acetate
  5. washThe ethyl acetate layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled away
  8. customthe residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:4-1:1)
  9. customrecrystallized from diisopropyl ether-hexane

출처 및 근거

ORD 기록
ord-80f17c6e023d4320b0ad93235976cfee
출처 데이터셋
uspto-grants-1998_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05719176

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