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Hydrochloric Acid → 1H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-3-oxo-8-[3-(2-pyridinylamino)propoxy]-2-(2,2,2-trifluoroethyl)-, (4S)-

HRID 2416741
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2416741
[O:1]=[C:2]1[C@H:8]([CH2:9][C:10]([O:12]C)=[O:11])[CH2:7][C:6]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:17][C:5]=2[CH2:4][N:3]1[CH2:29][C:30]([F:33])([F:32])[F:31].[OH-].[Na+].Cl>O1CCOCC1>[O:1]=[C:2]1[C@H:8]([CH2:9][C:10]([OH:12])=[O:11])[CH2:7][C:6]2[CH:14]=[CH:15][C:16]([O:18][CH2:19][CH2:20][CH2:21][NH:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=3)=[CH:17][C:5]=2[CH2:4][N:3]1[CH2:29][C:30]([F:33])([F:31])[F:32]
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Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10695472HCID 10695472, Verbindung

Produkt 1

HCID 99554611H-2-Benzazepine-4-acetic acid, 2,3,4,5-tetrahydro-3-oxo-8-[3-(2-pyridinylamino)propoxy]-2-(2,2,2-trifluoroethyl)-, (4S)-Ausbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 31275
1,4-Dioxane
Lösungsmittel

Versuchsvorschrift

To a stirred solution of methyl (S)-3-oxo-8-[3-(pyridin-2-ylamino)-1-propyloxy]-2-(2,2,2-trifluoroethyl)-2,3,4,5-tetrahydro-1H-2-benzazepine-4-acetate (19.50 g, 42 mmol) in dioxane (150 mL) was added aqueous 1 N NaOH (75 mL, 75 mmol). The cloudy reaction was stirred at RT for 2 h, then the resulting homogeneous solution was neutralized with aqueous 1 N HCl (75 mL, 75 mmol). The solution was concentrated to near dryness by rotary evaporation to precipitate out the product. The supernatant was decanted off and the remaining gummy solid was redissolved in methanol. The clear solution was then reconcentrated by rotary evaporation. The remaining solid was triturated with a small volume of water, filtered and dried under vacuum to give the title compound (16.38 g, 86%) as a white powder. HPLC (Hamilton PRP-1®, 25% CH3CN/H2O containing 0.1% TFA) k′=3.1; [α]D−112.3° (c, 1.0, MeOH); MS (ES) m/e 452.3 (M+H)+; 1H NMR (400 MHz, DMSO-d6) δ 7.95 (dd, 1H), 7.34 (dt, 1H), 7.02 (d, J=9.2 Hz, 1H), 6.81 (m, 2H), 6.58 (t, 1H), 6.47 (m, 2H), 5.30 (d, J=16.5 Hz, 1H), 4.27-4.13 (m, 2H), 4.15 (d, J=16.5 Hz, 1H), 4.02 (t, 1H), 3.78 (m, 1H), 3.37 (m, 2H), 3.00 (dd, 1 H), 2.69 (dd, 1H), 2.65 (dd, 1H), 2.41 (dd, 1H), 1.96 (ddd, 2 H). Anal. Calcd for C22H24F3N3O4: C, 58.53; H, 5.36; N, 9.31. Found: C, 58.37; H, 5.42; N, 9.20.

Aufarbeitung

  1. customThe cloudy reaction
  2. concentrationThe solution was concentrated
  3. customby rotary evaporation
  4. customto precipitate out the product
  5. customThe supernatant was decanted off
  6. dissolutionthe remaining gummy solid was redissolved in methanol
  7. customThe clear solution was then reconcentrated by rotary evaporation
  8. customThe remaining solid was triturated with a small volume of water
  9. filtrationfiltered
  10. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-832f355a31914a7a98e16c5b200875f4
Quelldatensatz
uspto-grants-2004_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06825188B2

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