Lithium Hydroxide → (S)-2-ethoxy-3-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acid

HRID 584911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 584911
C([C@H]1COC(=O)N1C(=O)[C@@H:15]([O:40][CH2:41][CH3:42])[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([CH3:39])[C:31](=[O:38])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:24]=2)=[CH:19][CH:18]=1)C1C=CC=CC=1.C1[CH2:48][O:47]CC1.[OH-:49].[Li+]>O>[CH2:41]([O:40][C@@H:15]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([CH2:29][N:30]([CH3:39])[C:31]([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)=[O:38])[CH:24]=2)=[CH:21][CH:22]=1)[C:48]([OH:47])=[O:49])[CH3:42]

Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 69694199N-{4'-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide

Produkt 1

HCID 10273463(S)-2-ethoxy-3-(3'-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acidAusbeute 47 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

600 mg (1 mmol) of N-{4′-[(S)-3-((S)-4-benzyl-2-oxooxazolidin-3-yl)-2-ethoxy-3-oxopropyl]biphenyl-3-ylmethyl}-N-methylbenzamide and 10 ml of THF are introduced into a round-bottomed flask. At 0° C., 4.2 ml (2 mmol) of an aqueous lithium hydroxide solution (0.5M) are added and the mixture is stirred for one hour. The reaction medium is poured into water, acidified to pH 1 and extracted with ethyl acetate, and the organic phase is separated out after settling of the phases has taken place, dried over magnesium sulfate and evaporated. The residue obtained is purified by chromatography on a column of silica eluted with a mixture of heptane and ethyl acetate (50/50). 200 mg (47%) of (S)-2-ethoxy-3-(3′-{[methyl-(1-phenylmethanoyl)amino]methyl}biphenyl-4-yl)propionic acid, with a melting point of 53-54° C., are obtained.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. customthe organic phase is separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. washeluted with a mixture of heptane and ethyl acetate (50/50)

Quellen und Nachweise

ORD-Eintrag
ord-5d4a5717dac2420fa4c5ecc8d083c066
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06927228B2

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