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Hydrogen Peroxide → HCID 68181133, Verbindung

HRID 2371298
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2371298
[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH:11]([C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:29][CH:28]=2)[C:12](N2[C@H](CC3C=CC=CC=3)COC2=O)=[O:13])=[CH:6][CH:5]=1.[OH:40]O.[Li+].[OH-]>C1COCC1.O>[CH3:1][O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C@@H:11]([C:12]([OH:13])=[O:40])[C:27]2[CH:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:29][CH:28]=2)=[CH:6][CH:5]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 67487803HCID 67487803, Verbindung

Produkt 1

HCID 68181133HCID 68181133, VerbindungAusbeute 134,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

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

Versuchsvorschrift

To a stirred solution of the (R)-diastereomer of 4-{3-(4-(R)-Benzyl-2-oxo-oxazolidin-3-yl)-2-[4-(3,3-dimethyl-but-1-enyl)-phenyl)-3-oxo-propyl}-benzoic acid methyl ester (0.43 g, 0.81 mmol) in THF/H2O (20 mL) (3:1) at room temperature were added H2O2 (2.2 mL, 8.1 mmol 35% in H2O) followed by LiOH (40 mg, 1.63 mmol). The reaction mixture was stirred for 3 h, at room temperature, quenched with (0.1 N HCl). The reaction mixture was extracted with ethyl acetate (100 mL) and dried over MgSO4, filtered and concentrated under reduced pressure to afford corresponding acid. The crude product was purified by column chromatography on silica gel, eluting with CH2Cl2/MeOH 2%-15% to afford the title compound (0.4 g, 100%).

Aufarbeitung

  1. customquenched with (0.1 N HCl)
  2. extractionThe reaction mixture was extracted with ethyl acetate (100 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto afford corresponding acid
  7. customThe crude product was purified by column chromatography on silica gel
  8. washeluting with CH2Cl2/MeOH 2%-15%

Quellen und Nachweise

ORD-Eintrag
ord-f5f33fe1dcb4491c9f585fec7614ca5c
Quelldatensatz
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08710236B2

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