StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Sodium hydride → benzyl 2-[(4R)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylate

HRID 232207
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 232207
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][NH:13][C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Cl[C:20]1([C:26]([O:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[O:27])[CH:24]=[CH:23][C:22](=[O:25])[O:21]1>CN(C)C=O.C(OCC)(=O)C.O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[CH2:15][O:14][N:13]([C:20]3([C:26]([O:28][CH2:29][C:30]4[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=4)=[O:27])[CH:24]=[CH:23][C:22](=[O:25])[O:21]3)[C:12]2=[O:16])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 3

HCID 24758Sodium hydrideHCID 20030939HCID 20030939, VerbindungHCID 54136951HCID 54136951, Verbindung

Produkt 1

HCID 67902028benzyl 2-[(4R)-4-phenylacetamido-3-oxo-2-isoxazolidinyl]-5-oxo-2,5-dihydro-2-furancarboxylateAusbeute 20,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittel
HCID 6228DimethylformamideLösungsmittel2×
HCID 8857Ethyl AcetateLösungsmittel2×

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

In 3 ml of anhydrous N,N-dimethylformamide was dissolved 220 mg of (4R)-4-phenylacetamido-3-isoxazolidinone. To the solution was added, under ice-cooling and stirring, 60 mg of sodium hydride (50% mineral oil), which was stirred for 10 minutes. Then the reaction solution was cooled to -10° C., to which was added under stirring 0.7 ml of anhydrous N,N-dimethylformamide solution dissolving 250 mg of the Compound (28) obtained in Example 28. The reaction solution was stirred at the same temperature for 45 minutes, followed by pouring into a mixture of ethyl acetate and water. The ethyl acetate layer was taken, washed with water and dried (Na2SO4). The solvent was evaporated off, and the residue was subjected to a silica gel column chromatography, followed by elution with hexane-ethyl acetate (2:1) to give 87 mg of the subject Compound (32) as colorless foamy substance.

Aufarbeitung

  1. additionTo the solution was added, under ice-
  2. temperaturecooling
  3. additionwas added
  4. stirringThe reaction solution was stirred at the same temperature for 45 minutes
  5. washwashed with water
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was evaporated off
  8. washfollowed by elution with hexane-ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-3ecab5ff10a34380a1fc4a9d4812e11c
Quelldatensatz
uspto-grants-1989_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04851422

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion