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

HRID 1009473
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1009473
[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]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8071
1,2-Dimethoxyethane
Lösungsmittel
2×
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d93ac78d7ca94471a7ca466614bbe07f
Quelldatensatz
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07973078B2

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