Lithium Hydroxide → HCID 11664670, Verbindung

HRID 1786554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1786554
C([O:3][C:4]([C@@H:6]1[CH2:10][C@H:9]([NH:11][C:12](=[O:32])[CH2:13][CH2:14][CH2:15][CH2:16][CH:17]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)[CH2:8][N:7]1[C:33](=[O:50])[C:34]1[CH:39]=[C:38]([C:40]([CH3:43])([CH3:42])[CH3:41])[C:37]([O:44][CH3:45])=[C:36]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:35]=1)=[O:5])C.[Li+].[OH-]>C1COCC1.CO.O>[F:24][C:21]1[CH:22]=[CH:23][C:18]([CH:17]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[CH2:16][CH2:15][CH2:14][CH2:13][C:12]([NH:11][C@@H:9]2[CH2:8][N:7]([C:33](=[O:50])[C:34]3[CH:39]=[C:38]([C:40]([CH3:41])([CH3:42])[CH3:43])[C:37]([O:44][CH3:45])=[C:36]([C:46]([CH3:49])([CH3:48])[CH3:47])[CH:35]=3)[C@H:6]([C:4]([OH:5])=[O:3])[CH2:10]2)=[O:32])=[CH:19][CH:20]=1

Komponenten

6

Edukt 2

HCID 3939Lithium HydroxideHCID 11707403HCID 11707403, Verbindung

Produkt 1

HCID 11664670HCID 11664670, VerbindungAusbeute 75,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To the solution of (2S,4S)-4-[6,6-Bis-(4-fluoro-phenyl)-hexanoylamino]-1-(3,5-di-tert-butyl-4-methoxy-benzoyl)-pyrrolidine-2-carboxylic acid ethyl ester (33) (0.32 g, 0.52 mmol) in THF (15 ml), MeOH (5 ml) and water (5 ml) was added LiOH (0.1 g, 2.45 mmol), and the reaction mixture was stirred at room temperature overnight. The reaction was then concentrated under reduced pressure. The residue was neutralized with 2N HCl to pH˜2 and dissolved in ethyl acetate: water (10:1) (150 ml). The organic was washed with water (30 ml, 2×), dried over MgSO4 and evaporated to dryness. The resulting residue was purified by column chromatography using CH2Cl2: MeOH (10:1) to give 0.26 g of desired product.

Aufarbeitung

  1. concentrationThe reaction was then concentrated under reduced pressure
  2. dissolutiondissolved in ethyl acetate: water (10:1) (150 ml)
  3. washThe organic was washed with water (30 ml, 2×)
  4. dry with materialdried over MgSO4
  5. customevaporated to dryness
  6. customThe resulting residue was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7f009c52032d459bb8dea3aedafca017
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07507760B2

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