Hydrochloric Acid → Diethyl 2-benzyloxycarbonylamino-2-(methoxycarbonylmethyl)malonate

HRID 57742

반응식

HRID 57742 반응식
[CH2:1]([O:8][C:9]([NH:11][CH:12]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[K+].Br[CH2:32][C:33]([O:35][CH3:36])=[O:34].Cl>CN(C=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH2:32][C:33]([O:35][CH3:36])=[O:34])([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:18]([O:20][CH2:21][CH3:22])=[O:19])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonate

생성물 1

HCID 66725236Diethyl 2-benzyloxycarbonylamino-2-(methoxycarbonylmethyl)malonate수율 95.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A suspension of diethyl 2-benzyloxycarbonylaminomalonate (3.0 g), potassium carbonate (1.6 g), potassium iodide (0.19 g), and methyl 2-bromoacetate (1.9 g) in DMF (50 mL) was stirred at 50° C. for 1 hour. The reaction mixture was cooled, and then poured into diluted hydrochloric acid, the mixture was extracted with ethyl acetate, and the extract was washed with saturated brine, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was subjected to silica gel column chromatography, in which elution was performed with n-hexane/ethyl acetate (4:1) for purification, and then crystallized from ethyl acetate/n-hexane to obtain the title compound (3.52 g, yield: 95%) as colorless oil.

후처리

  1. temperatureThe reaction mixture was cooled
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. washthe residue was subjected to silica gel column chromatography, in which elution
  7. customwas performed with n-hexane/ethyl acetate (4:1) for purification
  8. customcrystallized from ethyl acetate/n-hexane

출처 및 근거

ORD 기록
ord-995c581b90244a03a1e384a2adaad932
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434737B2

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