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Hydrochloric Acid → (5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)propoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydr oquinolin-5-ol

HRID 632612
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 632612
[F:1][C:2]1([F:64])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[C@@H:16]([O:18]CC4C=CC(OC)=CC=4)[CH2:15][C:14]([CH3:29])([CH3:28])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][C:39]([O:42][CH2:43][CH:44]5[CH2:49][O:48]C(C)(C)[O:46][CH2:45]5)=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[C@@H:52]([F:63])[C:53]2[CH:58]=[CH:57][C:56]([C:59]([F:62])([F:61])[F:60])=[CH:55][CH:54]=2)[CH2:4][CH2:3]1.Cl.C(=O)([O-])O.[Na+].[OH-].[Na+]>O1CCOCC1>[F:64][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[C@@H:16]([OH:18])[CH2:15][C:14]([CH3:28])([CH3:29])[CH2:13][C:12]=3[N:11]=[C:10]([CH:30]3[CH2:35][CH2:34][N:33]([C:36]4[N:41]=[CH:40][C:39]([O:42][CH2:43][CH:44]([CH2:49][OH:48])[CH2:45][OH:46])=[CH:38][N:37]=4)[CH2:32][CH2:31]3)[C:9]=2[C@@H:52]([F:63])[C:53]2[CH:58]=[CH:57][C:56]([C:59]([F:60])([F:62])[F:61])=[CH:55][CH:54]=2)[CH2:6][CH2:7]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 89683330(5S)-4-(4,4-Difluorocyclohexyl)-2-(1-{5-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]pyrimidin-2-yl}piperidin-4-yl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline

Produkt 1

HCID 71656703
(5S)-4-(4,4-Difluorocyclohexyl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-2-(1-{5-[3-hydroxy-2-(hydroxymethyl)propoxy]pyrimidin-2-yl}piperidin-4-yl)-7,7-dimethyl-5,6,7,8-tetrahydr oquinolin-5-ol
Ausbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 8.42 g (9.39 mmol) of (5S)-4-(4,4-Difluorocyclohexyl)-2-(1-{5-[(2,2-dimethyl-1,3-dioxan-5-yl)methoxy]pyrimidin-2-yl}piperidin-4-yl)-3-{(S)-fluoro[4-(trifluoromethyl)phenyl]methyl}-5-[(4-methoxybenzyl)oxy]-7,7-dimethyl-5,6,7,8-tetrahydroquinoline, which was prepared by a method similar to that of Reference Example 21, in 75 ml of 1,4-dioxane, 15 ml of 6 N hydrochloric acid was added, and the reaction mixture was stirred at 80° C. for 2 hours. After completion of the reaction, the reaction solution was poured into a mixed solution of saturated sodium hydrogencarbonate aqueous solution and 2 N sodium hydroxide aqueous solution and extracted with ethyl acetate three times. The obtained organic phases were combined, washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [n-hexane/ethyl acetate=60/40-30/70 (V/V)] and the fraction including the desired compound was concentrated under reduced pressure. The obtained residue was dissolved in ethyl acetate, then n-heptane was added thereto, and the precipitate was obtained by filtration to provide 5.72 g of the title compound as a white solid (yield: 83%).

Aufarbeitung

  1. customAfter completion of the reaction
  2. extractionextracted with ethyl acetate three times
  3. washwashed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. concentrationwas concentrated under reduced pressure
  7. dissolutionThe obtained residue was dissolved in ethyl acetate
  8. additionn-heptane was added
  9. customthe precipitate was obtained by filtration

Quellen und Nachweise

ORD-Eintrag
ord-e0f0651640644e5e9506fe16ea72d402
Quelldatensatz
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09321747B2

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