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Acetic Acid → Ciglitazone

HRID 475525
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 475525
CC(=NO)C(C)=NO.[BH4-].[Na+].[CH3:11][C:12]1([CH2:18][O:19][C:20]2[CH:33]=[CH:32][C:23]([CH:24]=[C:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C(O)(=O)C>O.[OH-].[Na+].C1COCC1.CN(C=O)C>[CH3:11][C:12]1([CH2:18][O:19][C:20]2[CH:33]=[CH:32][C:23]([CH2:24][CH:25]3[S:29][C:28](=[O:30])[NH:27][C:26]3=[O:31])=[CH:22][CH:21]=2)[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 4311764Sodium borohydrideHCID 579718655-(4-((1-Methylcyclohexyl)methoxy)benzylidene)thiazolidine-2,4-dioneHCID 135459645Dimethylglyoxime

Produkt 1

HCID 2750Ciglitazone

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14798
Sodium Hydroxide
Katalysator
HCID 962WaterLösungsmittel2×
HCID 21974620tetrahydrofuran N,N-dimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To the suspension containing CoCl2.6H2O (4.5 mg, 0.016 mmol) and dimethylglyoxime (70.1 mg, 0.6 mmol) in 10 ml of water, 4 drops of 1.0N NaOH and NaBH4 (384.6 mg, 10 mmol) were subsequently added. The mixture was cooled to 0° C., and 5-(4-((1-methylcyclohexyl)methoxy)benzylidene)thiazolidine-2,4-dione (1 g, 3.0 mmol) in 15 ml of THF-DMF (2:1) was then added thereto over 20 minutes. The mixture was stirred at room temperature for 18 hours, to which acetic acid was then added until the pH thereof reached about 6. The mixture was diluted with water, and extracted with ethyl acetate and water. The organic layer was washed with water several times, dried with anhydrous magnesium sulfate, filtered and solvent-evaporated. The residual oil was chromatographed on silica gel to afford 5-(4-((1-methylcyclohexyl)methoxy)benzyl)thiazolidine-2,4-dione (Derivative 112 of the above formula) as white solid (0.8 g, yield: 80%).

Aufarbeitung

  1. additionwere subsequently added
  2. additionwas then added until the pH
  3. extractionextracted with ethyl acetate and water
  4. washThe organic layer was washed with water several times
  5. dry with materialdried with anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customsolvent-evaporated
  8. customThe residual oil was chromatographed on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-37980f75a3e84fb8a0685a620fad8b39
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08637558B2

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