Sodium Carbonate → HCID 58714528, Verbindung

HRID 1242559Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1242559
[C:1]1([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:6]=[CH:5][C:4]([C:7]([N:9]2[CH2:13][C:12](=[N:14][O:15][CH3:16])[CH2:11][C@H:10]2[C:17]2[O:21][N:20]=[C:19]([CH:22]3[CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]3)[N:18]=2)=[O:8])=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O.C(Cl)Cl.C(=O)([O-])[O-].[Na+].[Na+]>>[CH3:16][O:15][N:14]=[C:12]1[CH2:11][C@@H:10]([C:17]2[O:21][N:20]=[C:19]([CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:18]=2)[N:9]([C:7]([C:4]2[CH:3]=[CH:2][C:1]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[CH:6][CH:5]=2)=[O:8])[CH2:13]1

Komponenten

4

Edukt 3

HCID 10340Sodium CarbonateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 58714504HCID 58714504, Verbindung

Produkt 1

HCID 58714528HCID 58714528, VerbindungAusbeute 80 %

Versuchsvorschrift

tert-butyl 4-{5-[(2S,4EZ)-1-([1,1′-biphenyl]-4-ylcarbonyl)-4-(methoxyimino)pyrrolidinyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate) (100 mg, 1.80 mmol) was treated with a 25% TFA/DCM solution at 0° C. for 1 hour. The reaction was then made basic with a sodium carbonate solution (10%) and extracted with DCM. The organic phases were combined and dried over magnesium sulfate and solvent removal afforded a residue which was purified by flash-chromatography using cyclohexane/ethylacetate (2/8) as eluent to give (3EZ,5S)-1-([1,1′-biphenyl]-4-ylcarbonyl)-5-[3-(4-piperidinyl)-1,2,4-oxadiazol-5-yl]-3-pyrrolidinone O-methyloxime as a mixture of E-/Z-isomers in 80% yield (96.1% purity by HPLC).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ae490ef08f614e7cae4d7c54d7ce2f95
Quelldatensatz
uspto-grants-2006_10
Patentnummer
US07115639B2

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