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Water → Ethyl 3-{[(tert-butoxycarbonyl)amino]methyl}cinnamate

HRID 1009473
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HRID 1009473 반응식
[H-].[Na+].C(OP([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(OCC)=O)C.[CH:17]([C:19]1[CH:20]=[C:21]([CH:31]=[CH:32][CH:33]=1)[CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=O.O>C(COC)OC.C(OCC)(=O)C>[C:26]([O:25][C:24]([NH:23][CH2:22][C:21]1[CH:20]=[C:19]([CH:33]=[CH:32][CH:31]=1)[CH:17]=[CH:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[O:30])([CH3:29])([CH3:27])[CH3:28]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 962WaterHCID 13345Triethyl phosphonoacetateHCID 24758Sodium hydrideHCID 2794834tert-Butyl 3-formylbenzylcarbamate

생성물 1

HCID 67304746Ethyl 3-{[(tert-butoxycarbonyl)amino]methyl}cinnamate

시약·촉매·용매 2

HCID 80711,2-Dimethoxyethane용매2회
HCID 8857Ethyl Acetate용매

실험 절차

374 mg of 60% sodium hydride was suspended in 20.0 mL of dimethoxyethane, and 1.91 g of ethyl diethylphosphonoacetate was added dropwise thereto at −5° C., followed by stirring at room temperature for 10 minutes. To the reaction liquid was added dropwise a solution of tert-butyl (3-formylbenzyl)carbamate in dimethoxyethane (5.00 mL), followed by stirring at 60° C. for 4 hours. The reaction liquid was cooled to room temperature, followed by addition of water and extraction with ethyl acetate. The organic layer was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain ethyl 3-{[(tert-butoxycarbonyl)amino]methyl}cinnamate. This was dissolved in 5.00 mL of ethyl acetate, and 8.50 mL of a 4 M hydrogen chloride/ethyl acetate solution was added thereto, followed by stirring at room temperature for 6 hours. The resulting precipitate was collected by filtration, washed with ethyl acetate, and then dried under reduced pressure to obtain 1.71 g of ethyl 3-(aminomethyl)cinnamate hydrochloride.

후처리

  1. customat −5° C.
  2. customTo the reaction liquid
  3. stirringby stirring at 60° C. for 4 hours
  4. customThe reaction liquid
  5. temperaturewas cooled to room temperature
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-d93ac78d7ca94471a7ca466614bbe07f
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07973078B2

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