Hydrogen Peroxide → (2R)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid

HRID 264942Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 264942
OO.C([C@@H]1COC(=O)N1[C:16](=[O:36])[C@H:17]([CH:33]([CH3:35])[CH3:34])[CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=1)C1C=CC=CC=1.[OH-].[Li+].S([O-])([O-])=[O:40].[Na+].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.O>[CH:33]([C@@H:17]([CH2:18][C:19]1[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([O:27][CH2:28][CH2:29][CH2:30][O:31][CH3:32])[CH:20]=1)[C:16]([OH:36])=[O:40])([CH3:34])[CH3:35]

Komponenten

7

Edukt 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 22865791(R)-4-Benzyl-3-((S)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)oxazolidin-2-one

Produkt 1

HCID 9944529(2R)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

0.434 litre of 30% hydrogen peroxide is slowly added to 300 g of 4(R)-benzyl-3-{2(S)-isopropyl-3-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-propionyl}-oxazolidin-2-one in 4.8 litres of tetrahydrofuran/water (3:1) at 0° C. After the addition of 31.2 g of lithium hydroxide, the mixture is stirred for 3 hours at 0°-20° C. 2.55 litres of 1.5M sodium sulfite solution are then added to the reaction mixture at 0°-15° C. and stirring is continued for a further 30 minutes. 1 litre of saturated sodium hydrogen carbonate solution is added and the tetrahydrofuran is evaporated off. The aqueous solution is washed repeatedly with dichloromethane and then acidified with 2N hydrochloric acid (pH 3.0). Extraction with dichloromethane and subsequent evaporation of the solvent yield the title compound: Rf (ethyl acetate/hexane=2:1)=0.30; m.p. 43.5°-44° C.

Aufarbeitung

  1. stirringstirring
  2. waitis continued for a further 30 minutes
  3. customthe tetrahydrofuran is evaporated off
  4. washThe aqueous solution is washed repeatedly with dichloromethane
  5. extractionExtraction
  6. customwith dichloromethane and subsequent evaporation of the solvent

Quellen und Nachweise

ORD-Eintrag
ord-7d6140ffc6784d9bbb3ce3050e20af49
Quelldatensatz
uspto-grants-1997_07
Patentnummer
US05646143

Notizen zur Reaktion

Wird geladen…