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Sodium Bicarbonate → HCID 70874808, Verbindung

HRID 2172270
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2172270
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1.[N+:13]([C:16]1[N:17]=[C:18]2[N:23]([CH:24]=1)[CH2:22][CH2:21][C@H:20]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][C:36](=O)[CH2:35][CH2:34]3)=[CH:29][CH:28]=1)[O:19]2)([O-:15])=[O:14].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(O)(=O)C.ClCCCl>[N+:13]([C:16]1[N:17]=[C:18]2[N:23]([CH:24]=1)[CH2:22][CH2:21][C@H:20]([CH2:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([N:33]3[CH2:38][CH2:37][CH:36]([NH:8][C:7]4[CH:9]=[CH:10][C:4]([O:3][C:2]([F:11])([F:12])[F:1])=[CH:5][CH:6]=4)[CH2:35][CH2:34]3)=[CH:29][CH:28]=1)[O:19]2)([O-:15])=[O:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 516892Sodium BicarbonateHCID 6008484-(Trifluoromethoxy)anilineHCID 5049666Sodium triacetoxyborohydrideHCID 70874615HCID 70874615, Verbindung

Produkt 1

HCID 70874808HCID 70874808, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11
1,2-Dichloroethane
Lösungsmittel
HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

4-(Trifluoromethoxy)aniline (1.271 ml) was added to a 1,2-dichloroethane solution (50 ml) of 1-[4-((R)-2-nitro-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazin-7-ylmethoxy)phenyl]piperidin-4-one (2.5 g). Subsequently, sodium triacetoxyborohydride (1.992 g) and acetic acid (0.538 ml) were added thereto and the mixture was stirred at room temperature for 21 hours. A saturated sodium hydrogen carbonate aqueous solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was washed with a saturated sodium chloride aqueous solution and dried over anhydrous sodium sulfate. Thereafter, the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1) and recrystallized from ethyl acetate to afford the title compound as a yellow powder (2.55 g).

Aufarbeitung

  1. extractionfollowed by extraction with methylene chloride
  2. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationThereafter, the solvent was distilled off under reduced pressure
  5. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate:n-hexane=1:1)
  6. customrecrystallized from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-19a9bb5aaf0a48089107a58fa2c7006c
Quelldatensatz
uspto-grants-2015_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09051333B2

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