Acetyl chloride → HCID 58714527, Verbindung

HRID 1242560Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242560
[CH3:1][O:2][N:3]=[C:4]1[CH2:8][C@@H:7]([C:9]2[O:13][N:12]=[C:11]([CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[N:10]=2)[N:6]([C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:24][CH:23]=2)=[O:21])[CH2:5]1.C(N(CC)CC)C.[C:41](Cl)(=[O:43])[CH3:42].C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)Cl>[CH3:1][O:2][N:3]=[C:4]1[CH2:8][C@@H:7]([C:9]2[O:13][N:12]=[C:11]([CH:14]3[CH2:19][CH2:18][N:17]([C:41](=[O:43])[CH3:42])[CH2:16][CH2:15]3)[N:10]=2)[N:6]([C:20]([C:22]2[CH:23]=[CH:24][C:25]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[CH:26][CH:27]=2)=[O:21])[CH2:5]1

Komponenten

6

Edukt 4

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 58714528HCID 58714528, Verbindung

Produkt 1

HCID 58714527HCID 58714527, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

(3EZ,5S)-1-([1,1′-biphenyl]-4-ylcarbonyl)-5-[3-(4-piperidinyl)-1,2,4-oxadiazol-5-yl]-3-pyrrolidinone O-methyloxime (Example 12) was dissolved in dry DCM at 0° C. in presence of 1.5 equivalent of triethyl amine and treated with 1 equivalent of acetyl chloride. The reaction mixture was stirred at this temperature for 30 minutes and then hydrolyzed with ice. The reaction was then made basic with a sodium carbonate solution (10%) and extracted with DCM. It was then dried with magnesium sulfate and solvent removal afforded a residue which was purified by flash-chromatography using cyclohexane/ethylacetate (1/1) as eluent to give (3EZ,5S)-5-[3-(1-acetyl-4-piperidinyl)-1,2,4-oxadiazol-5-yl]-1-([1,1′-biphenyl]-4-ylcarbonyl)-3-pyrrolidinone O-methyloxime as a mixture of E-/Z-isomers in 95% yield (100% purity by HPLC).

Aufarbeitung

  1. extractionextracted with DCM
  2. dry with materialIt was then dried with magnesium sulfate and solvent removal
  3. customafforded a residue which
  4. customwas purified by flash-chromatography

Quellen und Nachweise

ORD-Eintrag
ord-a3ad43c990f84a6f85f06616eb825647
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115639B2

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