Water → Ethyl 3-[(furan-2-ylmethyl)(ethoxycarbonyl)amino]propanoate

HRID 1511601Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1511601
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11].C(N(CC)CC)C.Cl[C:23]([O:25][CH2:26][CH3:27])=[O:24].O>C(Cl)Cl>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11]

Komponenten

6

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 2736426Ethyl 3-[(2-furylmethyl)amino]propanoate

Produkt 1

HCID 243303Ethyl 3-[(furan-2-ylmethyl)(ethoxycarbonyl)amino]propanoateAusbeute 93,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Ethyl 3-[(furan-2-ylmethyl)amino]propionate (10.8 g) prepared in the step 2 and 18.3 mL of triethylamine were dissolved in 180 mL of methylene chloride, 7.14 g of ethyl chloroformate was added by slowly dropping thereinto under cooling with ice and the mixture was stirred at room temperature for 5 hours. Water (200 mL) was added to the reaction solution and the mixture was subjected to extraction with methylene chloride. The organic layer was washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo therefrom. The residue was purified by silica gel column chromatography to give 13.77 g of the objective compound as yellow liquid.

Aufarbeitung

  1. temperatureunder cooling with ice
  2. extractionthe mixture was subjected to extraction with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-630b018dd7f74135a6e4f2b3ac4b8c1a
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217031B2

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