p-Toluenesulfonic acid monohydrate → HCID 178462393, compound

HRID 480948Notes

Reaction equation

HRID 480948 reaction equation
[Cl: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>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:6][C:7](=[O:16])[C:8]2[CH:13]=[CH:12][C:11]([C@H:14]3[O:39][CH2:38][C@H:37]([S:36][C@H:34]([CH3:35])[C@:27]([C:21]4[CH:22]=[CH:23][C:24]([F:26])=[CH:25][C:20]=4[F:19])([OH:42])[CH2:28][N:29]4[CH:33]=[N:32][CH:31]=[N:30]4)[CH2:40][O:15]3)=[CH:10][CH:9]=2)=[CH:17][CH:18]=1

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 114142744'-Chloro-4-formylbenzanilide

Product 1

HCID 178462393HCID 178462393, compoundYield 48.2%

Procedure

In the same manner as that described in Example 3(3) a reaction was carried out using 4′-chloro-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 (359 mg, 1.0 mmol) and p-toluenesulfonic acid monohydrate (342 mg, 1.8 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 (290 mg, yield 48%) as a colorless solid and the cis isomer (82 mg, yield 14%) 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-bc328da229b24a04ba2785887e3d6702
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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