Hydrochloric Acid → HCID 67468592, Verbindung

HRID 1519243Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1519243
C[O:2][C:3](=[O:32])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]2[N:13]=[C:14]([C:25]3[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=3)[O:15][C:16]=2[S:17][C:18]2[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][N:19]=2)=[CH:6][CH:5]=1.[Li+].[OH-].Cl>CO.C1COCC1.O>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([S:17][C:16]2[O:15][C:14]([C:25]3[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=3)=[N:13][C:12]=2[CH2:11][O:10][C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:32])=[O:2])=[CH:9][CH:8]=2)=[N:19][CH:20]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 71184062HCID 71184062, Verbindung

Produkt 1

HCID 67468592HCID 67468592, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of Methyl-4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)benzoate (0.31 g, 0.66 mmol) in 6 ml of 1:1 MeOH/THF was added 1N LiOH (1.98 ml, 1.98 mmol). The reaction was allowed to proceed at 55° C. for 2 h, at which point it was cooled to room temperature and was acidified by 3N HCl. The reaction mixture was diluted with water and extracted with EtOAc. The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to yield 4-({5-[(5-chloropyridin-2-yl)sulfanyl]-2-(4-fluorophenyl)-1,3-oxazol-4-yl}methoxy)benzoic acid as a white solid. It was used as is for the next step. LCMS [M+H]=457.3.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-af35ea163ca142bea981da9e5a6b51fc
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09073879B2

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