Water → HCID 21111446, Verbindung

HRID 425945Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 425945
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH2:27])=[C:14]([O:16][CH2:17][C:18]3[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=3[Cl:26])[CH:15]=2)=[CH:6][CH:5]=1.O.[Li+].[OH-]>C(O)(C)C.CCOC(C)=O.[Cl-].[Na+].O>[NH2:27][C:13]1[N:12]=[CH:11][C:10]([C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:28])=[O:2])=[CH:9][CH:8]=2)=[CH:15][C:14]=1[O:16][CH2:17][C:18]1[C:23]([F:24])=[CH:22][CH:21]=[C:20]([F:25])[C:19]=1[Cl:26]

Komponenten

7

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 66701762HCID 66701762, Verbindung

Produkt 1

HCID 21111446HCID 21111446, VerbindungAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3776IsopropanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

To a stirred solution of 4-[6-amino-5-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-3-yl]-benzoic acid methyl ester (2.5 g, 6 mmol) in warm isopropanol (300 mL) was added H2O (100 mL) containing LiOH (0.74 g, 31 mol). The reaction immediately turned orange and was left to stir at room temperature for 18 hr. The reaction was diluted with EtOAc (200 mL) and brine (50 mL). The organic was separated off and the aqueous was extracted with EtOAc (2×50 mL). The organic layers were combined and washed with brine (2×25 mL), dried with Na2SO4 and concentrated to dryness under vacuum to yield 4-[6-amino-5-(2-chloro-3,6-difluoro-benzyloxy)-pyridin-3-yl]-benzoic acid (2.4 g, 6 mmol, 99%) as an off-white solid.

Aufarbeitung

  1. customThe reaction immediately turned orange
  2. waitwas left
  3. customThe organic was separated off
  4. extractionthe aqueous was extracted with EtOAc (2×50 mL)
  5. washwashed with brine (2×25 mL)
  6. dry with materialdried with Na2SO4
  7. concentrationconcentrated to dryness under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-537abf7b8b3842fd9e3705906a701282
Quelldatensatz
uspto-grants-2012_01
Patentnummer
US08106197B2

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