Lithium Hydroxide → (S)-2-(2-Methoxyphenyl)propanoic acid

HRID 375422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 375422
[OH-].[Li+].C[C@H]1[C@H](C2C=CC=CC=2)OC(=O)N1[C:16](=[O:27])[C@H:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH3:26])[CH3:18].C(OCC)(=[O:30])C>O1CCCC1.O>[CH3:26][O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[C@H:17]([CH3:18])[C:16]([OH:27])=[O:30]

Komponenten

6

Edukt 3

HCID 3939Lithium HydroxideHCID 8857Ethyl AcetateHCID 54310187(4S,5S)-4-methyl5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]2-oxazolidinone

Produkt 1

HCID 11137716(S)-2-(2-Methoxyphenyl)propanoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

1.52 g of lithium hydroxide are added to a solution, cooled to +5° C., of 4.1 g of (4S,5S)-4-methyl-5-phenyl-3-[(S)-2-(2-methoxyphenyl)propionyl]-oxazolidin-2-one in 60 cm3 of tetrahydrofuran and 30 cm3 of water. The reaction mixture is stirred at this temperature for 3 hours and, after returning to room temperature, ethyl acetate is subsequently added, the mixture is decanted, the aqueous phase is acidified with an aqueous 1N solution of hydrochloric acid and extracted with ethyl acetate and the organic phase is dried over magnesium sulphate and concentrated to dryness under reduced pressure (2.7 kPa). The solid obtained is recrystallized from hexane, filtered off and dried. 0.4 g of (S)-2-(2-methoxyphenyl)propionic acid is obtained in the form of white crystals which melt at 102° C. [α]D20 =+84.6° (c=1; CHCl3).

Aufarbeitung

  1. customafter returning to room temperature
  2. customthe mixture is decanted
  3. extractionextracted with ethyl acetate
  4. dry with materialthe organic phase is dried over magnesium sulphate
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe solid obtained
  7. customis recrystallized from hexane
  8. filtrationfiltered off
  9. customdried

Quellen und Nachweise

ORD-Eintrag
ord-713f448867fd4ad69d65f77a5424c924
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05484804

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