Potassium Carbonate → (S)-N-{3-[4-(4-(Prop-2-yn-1-yl)-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide

HRID 1026670Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1026670
[Li][C:2]#[C:3][Si](C)(C)C.[O:8]=[C:9]1[CH2:14][CH2:13][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:11][CH2:10]1.[Cl-].[NH4+].[C:35](=O)([O-])[O-].[K+].[K+]>O1CCCC1>[CH2:35]([C:9]1([OH:8])[CH2:10][CH2:11][N:12]([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:25][C@H:24]([CH2:26][NH:27][C:28](=[O:30])[CH3:29])[O:23][C:22]3=[O:31])=[CH:17][C:16]=2[F:32])[CH2:13][CH2:14]1)[C:2]#[CH:3]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 54375226N-[(5S)-3-[3-fluoro-4-(4-oxopiperidinyl)phenyl]-2-oxo-5-oxazolidinyl]methylacetamideHCID 178506808HCID 178506808, Verbindung

Produkt 1

HCID 11749595(S)-N-{3-[4-(4-(Prop-2-yn-1-yl)-4-hydroxypiperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamideAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
78 °C

Versuchsvorschrift

A mixture of lithio(trimethylsilyl)acetylene (1.72 mmol) and (S)—N-{3-[4-(4-oxo-piperidin-1-yl)-3-fluorophenyl]-2-oxo-oxazolidin-5-ylmethyl}-acetamide (1.72 mmol) in tetrahydrofuran (10 ml) was stirred at a temperature—78° C. for 15 minutes. It was allowed to come to room temperature and further stirred for 18 hours. The reaction mixture was then stirred with aqueous solution of ammonium chloride, the reaction mixture was extracted with ethyl acetate (3×40 ml). The removal of the solvent provided a residue, which was stirred in aqueous methanolic (15 ml) solution of potassium carbonate (1.72 mmol) for 3 hours. The solvent was removed and the residual mass was purified by column chromatography over silica gel to provide title compound in 19% yield. M.P. 166-167° C. and MS (M+1)=376 (MH+, 100%) M.F.=C19H22FN3O4.

Aufarbeitung

  1. customto come to room temperature
  2. stirringfurther stirred for 18 hours
  3. extractionthe reaction mixture was extracted with ethyl acetate (3×40 ml)
  4. customThe removal of the solvent
  5. customprovided a residue, which
  6. customThe solvent was removed
  7. customthe residual mass was purified by column chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag
ord-247f63c77a014233bbc7514c526ed5ec
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08729269B2

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