p-Toluenesulfonic acid monohydrate → HCID 178462392, compound

HRID 480951Notes

Reaction equation

HRID 480951 reaction equation
[CH:1]([C:3]1[CH:21]=[CH:20][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2].[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C@:30]([OH:45])([C@H:37]([S:39][CH:40]([CH2:43]O)[CH2:41][OH:42])[CH3:38])[CH2:31][N:32]1[CH:36]=[N:35][CH:34]=[N:33]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:22][C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[C@@:30]([OH:45])([CH2:31][N:32]1[CH:36]=[N:35][CH:34]=[N:33]1)[C@H:37]([S:39][C@@H:40]1[CH2:41][O:42][C@@H:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:18])([F:17])[F:19])=[CH:12][CH:11]=3)=[O:8])=[CH:20][CH:21]=2)[O:2][CH2:43]1)[CH3:38]

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 187663494-Formyl-4'-(trifluoromethyl)benzanilide

Product 1

HCID 178462392HCID 178462392, compoundYield 47%

Procedure

In the same manner as that described in Example 3(3), a reaction was carried out using 4-formyl-4′-(trifluoromethyl)benzanilide (300 mg, 1.0 mmol), (2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (334 mg, 0.93 mmol) and p-toluenesulfonic acid monohydrate (318 mg, 1.7 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 (275 mg, yield 47%) as a white solid and the cis isomer (58 mg, yield 10%) 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-66f05593c70946a1821556a68a1a8d84
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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