Hydrochloric Acid → HCID 67354233, Verbindung

HRID 525216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525216
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][NH:12][C:13](=O)[CH2:14][C@H:15]2[CH2:19][CH2:18][N:17]([C:20]([CH:22]3[CH2:24][CH2:23]3)=[O:21])[CH2:16]2)=[O:10])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Cl>O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]([CH2:14][C@H:15]3[CH2:19][CH2:18][N:17]([C:20]([CH:22]4[CH2:24][CH2:23]4)=[O:21])[CH2:16]3)=[N:12][NH:11][C:9]2=[O:10])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 67354684HCID 67354684, Verbindung

Produkt 1

HCID 67354233HCID 67354233, VerbindungAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

In a round bottom flask equipped with reflux condenser, N-(4-bromophenyl)-2-{[(3R)-1-(cyclopropylcarbonyl)-3-pyrrolidinyl]acetyl}hydrazinecarboxamide (1.896 mmol) in water (75 mL) was treated with potassium carbonate (9.48 mmol). The resulting slurry was stirred at reflux overnight (15 h). The heating was turned off and the reaction was allowed to cool to room temperature. The pH was adjusted to ˜4 using 6N aq HCl. The aqueous solution was concentrated in vacuo to ˜50 mL, which was then extracted with ethyl acetate. The combined organic phases were washed with brine, dried over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography (0-10% methanol/dichloromethane). The fractions were concentrated in vacuo to provide the title compound as an off-white amorphous solid (65%). MS(ES)+ m/e 391.1, 393.2 [M+H]+.

Aufarbeitung

  1. customIn a round bottom flask equipped
  2. temperaturewith reflux condenser
  3. temperatureat reflux overnight (15 h)
  4. concentrationThe aqueous solution was concentrated in vacuo to ˜50 mL, which
  5. extractionwas then extracted with ethyl acetate
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude product was purified by flash chromatography (0-10% methanol/dichloromethane)
  11. concentrationThe fractions were concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-c506550c7a5f40e6983ca3d9eab16d0f
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340529B2

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