Water → HCID 54210532, Verbindung

HRID 1082192

Reaktionsgleichung

Reaktionsgleichung von HRID 1082192
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]2[CH2:15][CH2:14]2)[C@H:11]([C:16]([O:18]CC)=[O:17])[O:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].O>CO>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH:13]2[CH2:15][CH2:14]2)[C@H:11]([C:16]([OH:18])=[O:17])[O:10][CH:9]1[C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[CH:23][CH:22]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 53715740ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate

Produkt 1

HCID 54210532HCID 54210532, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 881 mg of ethyl (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylate (diastereomeric mixture) in 16 ml of methanol is added dropwise a solution of 64.7 mg of lithium hydroxide in 8 m 1 of water under cooling, and the mixture is stirred at room temperature for 1 hour. After the reaction mixture is evaporated under reduced pressure to remove methanol, the residue is dissolved in chloroform. The pH of the solution is adjusted to pH 2 with 10% hydrochloric acid. After extracted with chloroform, the extract is washed with brine twice, dried and evaporated to remove the solvent to give 792 mg of (4S,5R)-3-tert-butoxycarbonyl-2-(4-methoxyphenyl)-4-cyclopropyl-5-oxazolidinecarboxylic acid.

Aufarbeitung

  1. temperatureunder cooling
  2. customAfter the reaction mixture is evaporated under reduced pressure
  3. customto remove methanol
  4. dissolutionthe residue is dissolved in chloroform
  5. extractionAfter extracted with chloroform
  6. washthe extract is washed with brine twice
  7. customdried
  8. customevaporated
  9. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-1236fc2fa01d41c09833dab6b9e77e4e
Quelldatensatz
uspto-grants-1996_12
Patentnummer
US05589502

Verknüpfte Notizen

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