Sodium borohydride → HCID 67410837, Verbindung

HRID 2112200Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2112200
[BH4-].[Na+].C[O:4][C:5](=O)[C@@H:6]([NH:15][C:16]([C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][N:24]2[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:19]=1[O:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[F:39])=[O:17])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1>CO>[OH:4][CH2:5][C@@H:6]([NH:15][C:16]([C:18]1[CH:26]=[C:25]2[C:21]([CH:22]=[N:23][N:24]2[CH2:27][CH:28]([CH3:30])[CH3:29])=[CH:20][C:19]=1[O:31][C:32]1[CH:37]=[CH:36][C:35]([F:38])=[CH:34][C:33]=1[F:39])=[O:17])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]1

Komponenten

4

Edukt 2

HCID 4311764Sodium borohydrideHCID 67410827HCID 67410827, Verbindung

Produkt 1

HCID 67410837HCID 67410837, VerbindungAusbeute 44 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium borohydride (0.012 g, 0.31 mmol) was added portion-wise to a heated (50° C.) solution of (S)-2-{[5-(2,4-difluoro-phenoxy)-1-isobutyl-1H-indazole-6-carbonyl]-amino}-4-piperidin-1-yl-butyric acid methyl ester (0.022 g, 0.042 mmol) in MeOH. The reaction mixture was stirred at 50° C. until HPLC analysis showed consumption of the starting material. The mixture was cooled to room temperature and concentrated under reduced pressure. The residue was diluted with ethyl acetate and 1N HCl. The organics were extracted with 1N HCl until the organic layer contained no product by HPLC analysis. The aqueous solution was basified to pH 14 with NaOH and then extracted with dichloromethane several times. The combined organics were dried over MgSO4 and concentrated under reduced pressure to afford 9.1 mg of oil (44% yield). MS (APCI+) m/z 501 (M+1) detected.

Aufarbeitung

  1. customconsumption of the starting material
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated under reduced pressure
  4. additionThe residue was diluted with ethyl acetate and 1N HCl
  5. extractionThe organics were extracted with 1N HCl until the organic layer
  6. extractionextracted with dichloromethane several times
  7. dry with materialThe combined organics were dried over MgSO4
  8. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8c30433dae504dc885264183692dac21
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521447B2

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