Sodium Hydroxide → HCID 178525553, Verbindung

HRID 632939Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632939
[OH-].[Na+].C[O:4][C:5](=[O:42])[CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]2[CH:18]=[CH:17][C:16]([NH:19][C:20](=[O:41])[CH2:21][CH2:22][NH:23][C:24]([C:26]3[C:27]([C:37]([F:40])([F:39])[F:38])=[N:28][N:29]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[CH:30]=3)=[O:25])=[CH:15][CH:14]=2)[CH2:9][CH2:8]1>C1COCC1.CO.O>[C:31]1([N:29]2[CH:30]=[C:26]([C:24]([NH:23][CH2:22][CH2:21][C:20]([NH:19][C:16]3[CH:15]=[CH:14][C:13]([C@H:10]4[CH2:9][CH2:8][C@H:7]([CH2:6][C:5]([OH:42])=[O:4])[CH2:12][CH2:11]4)=[CH:18][CH:17]=3)=[O:41])=[O:25])[C:27]([C:37]([F:40])([F:39])[F:38])=[N:28]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 178500671HCID 178500671, Verbindung

Produkt 1

HCID 178525553HCID 178525553, VerbindungAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21892291Methanol tetrahydrofuran waterLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

NaOH (71.9 mg, 1.8 mmol) was added to trans-[4-(4-{3-[(1-phenyl-3-trifluoromethyl-1H-pyrazole-4-carbonyl)amino]propionylamino}phenyl)cyclohexyl]acetic acid methyl ester (100 mg, 0.18 mmol) dissolved in THF/MeOH/water (25 mL, 3:2:1). The reaction mixture was stirred at 25° C. for 5 hours and concentrated under vacuum. The residue was acidified with 1M HCl up to pH of 2 and extracted with ethyl acetate. The extract was washed with brine and dried with anhydrous sodium sulfate and concentrated under vacuum. Acetonitrile was added thereto and cooled to obtain a filtrate, and the filtrate was filtered and separated to obtain the desired compound (95 mg, 98%) as a white solid.

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with brine
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. additionAcetonitrile was added
  7. temperaturecooled
  8. customto obtain a filtrate
  9. filtrationthe filtrate was filtered
  10. customseparated

Quellen und Nachweise

ORD-Eintrag
ord-3977dc5341954b7a89d7adbf4f4f1267
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321728B2

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