Hydrochloric Acid → Diethyl 2-benzyloxycarbonylamino-2-(t-butoxycarbonylmethyl)malonate

HRID 57744

반응식

HRID 57744 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+].Br[CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32].Cl>CN(C=O)C.[I-].[K+]>[CH2:1]([O:8][C:9]([NH:11][C:12]([CH2:30][C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])([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 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 259787Diethyl 2-(benzyloxycarbonylamino)malonate

생성물 1

HCID 66725345Diethyl 2-benzyloxycarbonylamino-2-(t-butoxycarbonylmethyl)malonate수율 100.8%

시약·촉매·용매 2

HCID 4875Potassium Iodide촉매HCID 6228Dimethylformamide용매

반응 조건

온도
50 °C

실험 절차

A suspension of diethyl 2-benzyloxycarbonylaminomalonate (5.0 g), potassium carbonate (2.7 g), potassium iodide (0.27 g), and t-butyl 2-bromoacetate (4.1 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, and then purification was performed with n-hexane/ethyl acetate (5:1), to obtain the title compound (6.9 g, yield: 99%) 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. custompurification

출처 및 근거

ORD 기록
ord-90797a7338924070b568b0d13d20c8a2
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434737B2

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