Sodium Hydroxide → Efinaconazole

HRID 53663

Reaktionsgleichung

Reaktionsgleichung von HRID 53663
C1(C)C=CC(S([O:10][C@@:11]([C:27]2[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=2[F:34])([C@H:18]([N:20]2[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]2)[CH3:19])[CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)(=O)=O)=CC=1.[OH-].[Na+]>C(OCC)C>[F:34][C:28]1[CH:29]=[C:30]([F:33])[CH:31]=[CH:32][C:27]=1[C@:11]([OH:10])([C@H:18]([N:20]1[CH2:25][CH2:24][C:23](=[CH2:26])[CH2:22][CH2:21]1)[CH3:19])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1

Komponenten

4

Edukt 2

HCID 14798Sodium HydroxideHCID 88342129(2R, 3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidino)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol p-toluenesulfonate

Produkt 1

HCID 489181EfinaconazoleAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

To 18.3 g of the p-toluenesulfonate obtained above there were added 40 ml of ethyl ether and 35 ml of 1N aqueous solution of sodium hydroxide. The organic phase was taken out, and dried over 5 g of anhydrous magnesium sulfate and then the solvent was removed. There was added 40 ml of n-hexane to the residual liquid, and the precipitated crystal was separated by filtration, and dried to obtain 9.43 g of the desired (2R,3R)-2-(2,4-difluorophenyl)-3-(4-methylenepiperidine-1-yl)-1-(1H-1,2,4-triazole-1-yl)butane-2-ol. 1H-NMR spectrum of this compound coincided with that of the compound in Example 1.

Aufarbeitung

  1. dry with materialdried over 5 g of anhydrous magnesium sulfate
  2. customthe solvent was removed
  3. additionThere was added 40 ml of n-hexane to the residual liquid
  4. customthe precipitated crystal was separated by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-95f26bcfff1f42f7ba8d95bf590a9d25
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05620994

Verknüpfte Notizen

Wird geladen…