Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 53893355, Verbindung

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Reaktionsgleichung

[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]([OH:26])([C@H:17]([O:19]C1CCCCO1)[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C@:10]([OH:26])([C@H:17]([OH:19])[CH3:18])[CH2:11][N:12]1[CH:16]=[N:15][CH:14]=[N:13]1

Komponenten

Reaktionsbedingungen

Temperatur: 55 °C

Versuchsvorschrift

A mixture of (3R)-2-(2,4,5-trifluorophenyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (740 mg) and pyridinium p-toluene sulfonate (PPTS) 200 mg in ethanol (15 ml) was heated at 55° C. for 7 h. The reaction mixture was partitioned between ethyl acetate and water. The water layer was extracted with ethyl acetate. The combined organic extracts were dried over anhydrous magnesium sulfate, and concentrated to dryness in vacuo. Purification of the residue by silica gel chromatography (using dichloromethane:methanol=20:1 as an eluent) gave (2R,3R)-2-(2,4,5-trifluorophenyl)-1-(1H-1,2,4-triazol-1-yl)-2,3-butanediol (361 mg, 63%) as white amorphous.

Aufarbeitung

customThe reaction mixture was partitioned between ethyl acetate and water
extractionThe water layer was extracted with ethyl acetate
dry with materialThe combined organic extracts were dried over anhydrous magnesium sulfate
concentrationconcentrated to dryness in vacuo
customPurification of the residue by silica gel chromatography (

Quellen und Nachweise

ORD-Eintrag: ord-b1a9bbe5e34e4bfb9603a3f1c91e60cd
Quelldatensatz: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06300353B1

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