p-Toluenesulfonic acid monohydrate → HCID 178462400, compound

HRID 480949Notes

Reaction equation

HRID 480949 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:5]([NH:6][C:7](=[O:16])[C:8]2[CH:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C@:27]([OH:42])([C@H:34]([S:36][CH:37]([CH2:40]O)[CH2:38][OH:39])[CH3:35])[CH2:28][N:29]1[CH:33]=[N:32][CH:31]=[N:30]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:19][C:20]1[CH:25]=[C:24]([F:26])[CH:23]=[CH:22][C:21]=1[C@@:27]([OH:42])([CH2:28][N:29]1[CH:33]=[N:32][CH:31]=[N:30]1)[C@H:34]([S:36][C@@H:37]1[CH2:38][O:39][C@@H:14]([C:11]2[CH:12]=[CH:13][C:8]([C:7]([NH:6][C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:18][CH:17]=3)=[O:16])=[CH:9][CH:10]=2)[O:15][CH2:40]1)[CH3:35]

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 18766355N-(4-Fluorophenyl)-4-formylbenzamide

Product 1

HCID 178462400HCID 178462400, compoundYield 48%

Procedure

In the same manner as that described in Example 3(3), a reaction was carried out using 4′-fluoro-4-formylbenzanilide (300 mg, 1.2 mmol), (2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (385 mg, 1.1 mmol) and p-toluenesulfonic acid monohydrate (366 mg, 1.9 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 (306 mg, yield 48%) as a colorless oil and the cis isomer (78 mg, yield 12%) 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-db36d0d8a101474a8bc5ca1b1ea3b544
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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