Trifluoroacetic acid → HCID 18187489, Verbindung

HRID 1357911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1357911
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:20][CH2:19][CH:18]([CH2:21][CH2:22][C:23]([F:31])([F:30])[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:17][CH2:16]1)=O)(C)(C)C.C(=O)(O)[O-].[Na+].[OH-].[Na+]>C(Cl)Cl.O.[Cl-].[Na+].O.CCOCC>[F:31][C:23]([F:30])([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:22][CH2:21][CH:18]1[CH2:17][CH2:16][NH:15][CH2:20][CH2:19]1

Komponenten

9

Edukt 4

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 18187485HCID 18187485, Verbindung

Produkt 1

HCID 18187489HCID 18187489, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Trifluoroacetic acid (2.5 mL, 3.7 g, 32 mmol) was added dropwise to a solution of 1-(t-butoxycarbonyl)4-(3,3-difluoro-3-phenylprop-1-yl)piperidine from Step C (42 mg, 0.12 mmol) in methylene chloride (2.5 mL) at 0° C. After 80 min., the solution was transferred using a double-ended needle to a rapidly stirred solution of sodium bicarbonate (5.0 g, 60 mmol) in water (50 mL). Ether (50 mL) and 2.5 N aq. NaOH (20 mL) were added, followed by solid brine to saturate the aqueous layer. The aqueous layer was separated and extracted with ether (50 mL). The organic layers were washed in succession with saturated aq. brine (20 mL), combined, dried (sodium sulfate), decanted, and evaporated to give the title compound as 27 mg of colorless oil.

Aufarbeitung

  1. concentrationto saturate the aqueous layer
  2. customThe aqueous layer was separated
  3. extractionextracted with ether (50 mL)
  4. washThe organic layers were washed in succession with saturated aq. brine (20 mL)
  5. dry with materialdried (sodium sulfate)
  6. customdecanted
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3d87d377d24d4c0bb46bf3007f1e0a1a
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06593346B2

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