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

HRID 1009473
ノート
印刷プレビュー

反応式

HRID 1009473 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 80711,2-Dimethoxyethane溶媒2 回
HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d93ac78d7ca94471a7ca466614bbe07f
出典データセット
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07973078B2

反応ノート

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