p-Toluenesulfonic acid monohydrate → HCID 178462405, compound

HRID 480958Notes

Reaction equation

HRID 480958 reaction equation
[CH:1]([C:3]1[CH:17]=[CH:16][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2].[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C@:26]([OH:41])([C@H:33]([S:35][CH:36]([CH2:39]O)[CH2:37][OH:38])[CH3:34])[CH2:27][N:28]1[CH:32]=[N:31][CH:30]=[N:29]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:18][C:19]1[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=1[C@@:26]([OH:41])([CH2:27][N:28]1[CH:32]=[N:31][CH:30]=[N:29]1)[C@H:33]([S:35][C@@H:36]1[CH2:37][O:38][C@@H:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]3[CH:11]=[CH:12][N:13]=[CH:14][CH:15]=3)=[O:8])=[CH:16][CH:17]=2)[O:2][CH2:39]1)[CH3:34]

Participants

4

Reactant 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 18766377HCID 18766377, compound

Product 1

HCID 178462405HCID 178462405, compoundYield 37.4%

Procedure

In the same manner as that described in Example 3(3), a reaction was carried out using 4-formyl-N-(4-pyridyl)benzamide (200 mg, 0.88 mmol), (2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (318 mg, 0.88 mmol) and p-toluenesulfonic acid monohydrate (469 mg, 2.5 mmol) and the reaction mixture was treated according to a similar procedure to that described in Example 3(3) to give the trans isomer of the title compound (187 mg, yield 37%) as a white solid and the cis isomer (86 mg, yield 17%) as a colorless oil. The trans isomer was recrystallized from ethyl acetate-hexane to give white powdery crystals.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-89f362a1b262463d9b6c6f0f120a6703
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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