p-Toluenesulfonic acid monohydrate → HCID 178497886, Verbindung

HRID 480943

Reaktionsgleichung

Reaktionsgleichung von HRID 480943
[F:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[CH:12]=[O:13])[C:5]([O:7][CH3:8])=[O:6].[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C@:22]([OH:37])([C@H:29]([S:31][CH:32]([CH2:35][OH:36])[CH2:33][OH:34])[CH3:30])[CH2:23][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C@@:22]([OH:37])([CH2:23][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[C@H:29]([S:31][C@@H:32]1[CH2:33][O:34][C@@H:12]([C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[F:1])[O:13][CH2:35]1)[CH3:30].[F:14][C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[C@@:22]([OH:37])([CH2:23][N:24]1[CH:28]=[N:27][CH:26]=[N:25]1)[C@H:29]([S:31][C@H:32]1[CH2:33][O:34][C@@H:12]([C:11]2[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=2[F:1])[O:36][CH2:35]1)[CH3:30]

Komponenten

5

Edukt 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 10594623(2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]-thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanolHCID 18766342Methyl 3-fluoro-4-formylbenzoate

Produkt 2

HCID 178497885HCID 178497885, VerbindungAusbeute 10 %HCID 178497886HCID 178497886, VerbindungAusbeute 35 %

Versuchsvorschrift

In the same manner as that described in Example 3(3), a reaction was carried out using methyl 3-fluoro-4-formylbenzoate (105 mg, 0.58 mmol) obtained in Example 5(1), (2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (207 mg, 0.58 mmol) and p-toluenesulfonic acid monohydrate (199 mg, 1.04 mmol) and the reaction mixture was treated according to a similar procedure to that described in Example 3(3) to give methyl 4-[trans-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]-3-fluorobenzoate (trans isomer, 106 mg, yield 35%) and methyl 4-[cis-5-[[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl)propyl]thio]-1,3-dioxan-2-yl]-3-fluorobenzoate (cis isomer, 29 mg, yield 10%) as a colorless oil.

Aufarbeitung

  1. additionthe reaction mixture was treated

Quellen und Nachweise

ORD-Eintrag
ord-b12929c4ad864fc590412acb99fba096
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06653330B2

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