Lithium hydroxide, monohydrate → HCID 67297078, Verbindung

HRID 1807124Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807124
C[O:2][C:3](=[O:41])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]([C@H:13]2[C@H:17]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([Cl:24])[C:19]=3[F:25])[C@:16]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[F:35])([C:26]#[N:27])[C@H:15]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[NH:14]2)=[O:12])[CH2:7][CH2:6]1.O[Li].O>CO.O>[ClH:24].[Cl:24][C:20]1[C:19]([F:25])=[C:18]([C@@H:17]2[C@:16]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][C:29]=3[F:35])([C:26]#[N:27])[C@H:15]([CH2:36][C:37]([CH3:40])([CH3:39])[CH3:38])[NH:14][C@H:13]2[C:11]([N:8]2[CH2:7][CH2:6][CH:5]([CH2:4][C:3]([OH:41])=[O:2])[CH2:10][CH2:9]2)=[O:12])[CH:23]=[CH:22][CH:21]=1

Komponenten

5

Edukt 2

HCID 168937Lithium hydroxide, monohydrateHCID 59249477HCID 59249477, Verbindung

Produkt 1

HCID 67297078HCID 67297078, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a stirred solution of rac {1-[(2R,3S,4R,5S)-3-(3-Chloro-2-fluoro-phenyl)-4-(4-chloro-2-fluoro-phenyl)-4-cyano-5-(2,2-dimethyl-propyl)-pyrrolidine-2-carbonyl]-piperidin-4-yl}-acetic acid methyl ester (556 mg, 0.92 mmol) in methanol (8 mL), LiOH.H2O (Aldrich, 80 mg) in 1 mL of water was added. The mixture was stirred at 60° C. overnight. The reaction was quenched with addition of water. The mixture was filtered and the filtrate was concentrated to removed methanol. The aqueous layer was washed with EtOAc (2×5 mL) and acidified with 3N HCl. The mixture was then extracted with EtOAc (3×6 mL). The extracts were combined and dried over sodium sulfate and concentrated to give a white solid. 649 mg.

Aufarbeitung

  1. customThe reaction was quenched with addition of water
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customto removed methanol
  5. washThe aqueous layer was washed with EtOAc (2×5 mL)
  6. extractionThe mixture was then extracted with EtOAc (3×6 mL)
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a white solid

Quellen und Nachweise

ORD-Eintrag
ord-d55a56819ec048738cb97d287a1089e9
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08354444B2

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