2-Aminopropanol → ethyl 2-(3-acetyloxy-2,4,5-trifluorobenzoyl)-3-(1-hydroxypropan-2-ylamino)prop-2-enoate

HRID 1762318

Reaktionsgleichung

Reaktionsgleichung von HRID 1762318
[C:1]([O:4][C:5]1[C:6]([F:21])=[C:7]([CH:16]=[C:17]([F:20])[C:18]=1[F:19])[C:8]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[O:9])(=[O:3])[CH3:2].[C:22](OC(=O)C)(=O)C.[CH3:29][CH:30]([NH2:33])[CH2:31][OH:32]>ClCCl>[CH2:14]([O:13][C:11](=[O:12])[C:10]([C:8](=[O:9])[C:7]1[CH:16]=[C:17]([F:20])[C:18]([F:19])=[C:5]([O:4][C:1](=[O:3])[CH3:2])[C:6]=1[F:21])=[CH:22][NH:33][CH:30]([CH3:29])[CH2:31][OH:32])[CH3:15]

Komponenten

5

Edukt 3

HCID 51262-AminopropanolHCID 7918Acetic AnhydrideHCID 13934696Ethyl 3-acetoxy-2,4,5-trifluorobenzoylacetate

Produkt 1

HCID 178472010ethyl 2-(3-acetyloxy-2,4,5-trifluorobenzoyl)-3-(1-hydroxypropan-2-ylamino)prop-2-enoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To 7.64 g (0.025 mole) of the ethyl 3-acetoxy-2,4,5-trifluorobenzoylacetate (VIII) thus obtained were added 20 ml of acetic anhydride and 6 ml of ortho-ethyl formate and the mixture was refluxed for 2 hours and then condensed under reduced pressure. The residue was dissolved in 50 ml of dichloromethane, added 1.91 g (0.026 mole) of DL-2-aminopropanol and allowed to stand over night. Dichloromethane was distilled under reduced pressure and the residue was applied to silica gel column chromatography (solvent: mixture of toluene:ethyl acetate=1:1) to give 4.37 g of the ethyl-2-(3-acetoxy-2,4,5-trifluorobenzoyl)-3-(2-hydroxy-1-methylethyl)aminoacrylate (X) as pale yellow oily product. ##STR10##

Aufarbeitung

  1. temperaturethe mixture was refluxed for 2 hours
  2. customcondensed under reduced pressure
  3. waitto stand over night
  4. distillationDichloromethane was distilled under reduced pressure
  5. additionthe residue was applied to silica gel column chromatography (solvent: mixture of toluene:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-5fc6f5b5d4d840d8820924c181fb5983
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04831190

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