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Tetrabutylammonium Fluoride Trihydrate → tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-(2-hydroxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 339064
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 339064
C[C@:2]1([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:6][CH2:5][N:4]([C@@H:7]([C:12]2[CH:13]=[CH:14][C:15]3[N:16]([C:18]([C:21]4[CH:30]=[CH:29][C:28]5[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][O:34]C)=[CH:26][CH:27]=5)[N:22]=4)=[N:19][N:20]=3)[CH:17]=2)[C:8]([F:11])([F:10])[F:9])[CH2:3]1.O.O.O.[F-:47].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[F:9][C:8]([F:11])([F:10])[C@H:7]([N:4]1[CH2:5][CH2:6][C@H:2]([NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])[CH2:3]1)[C:12]1[CH:13]=[CH:14][C:15]2[N:16]([C:18]([C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][C:25]([O:31][CH2:32][CH2:33][OH:34])=[C:26]([F:47])[CH:27]=4)[N:22]=3)=[N:19][N:20]=2)[CH:17]=1
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Komponenten

4

Edukt 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 86707539tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Produkt 1

HCID 86707460tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-(2-hydroxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamateAusbeute 88,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a stirred solution of tert-butyl (S)-3-methyl-1-((S)-2,2,2-trifluoro-1-(3-(7-(2-methoxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (1.37 g, 1.94 mmol) in THF (100 mL) was added tetrabutylammonium fluoride trihydrate (1.84 g, 5.83 mmol). The reaction mixture was stirred at ambient temperature for 2 hours. The mixture was partitioned between saturated aqueous NH4Cl solution and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were washed with water and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3% MeOH in EtOAc) to give tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-(2-hydroxyethoxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (1.01 g, 88%) as a white solid.

Aufarbeitung

  1. customThe mixture was partitioned between saturated aqueous NH4Cl solution and EtOAc
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washThe combined organic layers were washed with water and brine
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography on silica gel (3% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-43725803dc854b92babb7ad55f0ed59f
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08889704B2

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