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Potassium Hydroxide → HCID 49846224, Verbindung

HRID 1930156
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1930156
[OH-].[K+].[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([N:27]4[CH2:32][CH2:31][CH:30]([C:33]([O:35]CC)=[O:34])[CH2:29][CH2:28]4)=[O:26])=[CH:20][C:19]=3[Cl:38])=[CH:14][CH:13]=2)[C:9]([CH3:39])=[N:8][C:7]=1[CH3:40])(=[O:5])[NH2:4]>CC(O)(C)C>[C:3]([C:6]1[N:11]=[C:10]([C:12]2[CH:13]=[CH:14][C:15]([C:18]3[CH:23]=[CH:22][C:21]([CH2:24][C:25]([N:27]4[CH2:28][CH2:29][CH:30]([C:33]([OH:35])=[O:34])[CH2:31][CH2:32]4)=[O:26])=[CH:20][C:19]=3[Cl:38])=[CH:16][CH:17]=2)[C:9]([CH3:39])=[N:8][C:7]=1[CH3:40])(=[O:5])[NH2:4]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 14797Potassium HydroxideHCID 59627658HCID 59627658, Verbindung2×

Produkt 1

HCID 49846224HCID 49846224, VerbindungAusbeute 21,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

Potassium hydroxide (91 mg, 1.63 mmol) was added in one portion to ethyl 1-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetyl)piperidine-4-carboxylate (Intermediate 19-1; 290.7 mg, 0.54 mmol) in t-BuOH (3505 μL) at RT. The resulting solution was stirred at 45° C. for 5 hours a precipitate formed. The reaction mixture was quenched with 2M HCl (5 mL), The reaction mixture was evaporated to dryness and redissolved in water (10 mL), and filtered through nylon, washed with water and dried under vacuum. The crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 50 mm diameter, 150 mm length), using decreasingly polar mixtures of water (containing 0.1% formic acid) and MeCN as eluents. Fractions containing the desired compound were evaporated to dryness to afford 1-(2-(4′-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)-2-chlorobiphenyl-4-yl)acetyl)piperidine-4-carboxylic acid (59.8 mg, 21.71%) as a white solid.

Aufarbeitung

  1. customformed
  2. customThe reaction mixture was quenched with 2M HCl (5 mL)
  3. customThe reaction mixture was evaporated to dryness
  4. dissolutionredissolved in water (10 mL)
  5. filtrationfiltered through nylon
  6. washwashed with water
  7. customdried under vacuum
  8. customThe crude product was purified by preparative HPLC (Waters XBridge Prep C18 OBD column, 5μ silica, 50 mm diameter, 150 mm length)
  9. additionFractions containing the desired compound
  10. customwere evaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-8030357754c745109c9eebef432f4c60
Quelldatensatz
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08188092B2

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