Trifluoroacetic acid → HCID 59625435, Verbindung

HRID 2192852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2192852
[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([CH2:45][CH:46]([CH3:48])[CH3:47])[C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:37][CH2:36][C:31]4([O:35][CH2:34][CH2:33][O:32]4)[CH2:30][CH2:29]3)=[O:27])[CH2:23][N:22](C(OC(C)(C)C)=O)[CH2:21]2)=[O:18])=[CH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].C(O)(C(F)(F)F)=O.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:5]1[N:10]=[C:9]([NH:11][CH2:12][CH2:13][CH2:14][O:15][CH3:16])[C:8]([C:17]([N:19]([C@H:20]2[CH2:25][C@@H:24]([C:26]([N:28]3[CH2:37][CH2:36][C:31]4([O:35][CH2:34][CH2:33][O:32]4)[CH2:30][CH2:29]3)=[O:27])[CH2:23][NH:22][CH2:21]2)[CH2:45][CH:46]([CH3:48])[CH3:47])=[O:18])=[CH:7][N:6]=1)([CH3:3])([CH3:4])[CH3:2]

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 59625248HCID 59625248, Verbindung

Produkt 1

HCID 59625435HCID 59625435, VerbindungAusbeute 47,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

tert-Butyl (3S,5R)-3-[({2-tert-butyl-4-[(3-methoxypropyl)amino]pyrimidin-5-yl}carbonyl)(2-methylpropyl)amino]-5-(1,4-dioxa-8-azaspiro[4.5]dec-8-ylcarbonyl)piperidine-1-carboxylate (72 mg) was dissolved in acetonitrile (8 ml), TFA (2 ml) was added and the mixture was stirred at room temperature for 3 hr. The reaction mixture was poured into 25% aqueous potassium carbonate solution at 0° C., and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to reversed-phase preparative HPLC, and fractions eluted with water-acetonitrile (9:1) to acetonitrile were collected. The mixture was basified (pH 10) with saturated aqueous potassium carbonate solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the object compound (29 mg).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. washeluted with water-acetonitrile (9:1) to acetonitrile
  6. customwere collected
  7. extractionthe mixture was extracted with ethyl acetate
  8. dry with materialThe extract was dried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-9420194980e8422080fce6096348ae28
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08329691B2

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