p-Toluenesulfonic acid monohydrate → HCID 178462407, compound

HRID 480970Notes

Reaction equation

HRID 480970 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][C:10]2[S:11][CH:12]=[CH:13][N:14]=2)=[O:8])=[CH:5][CH:4]=1)=[O:2].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@:25]([OH:40])([C@H:32]([S:34][CH:35]([CH2:38]O)[CH2:36][OH:37])[CH3:33])[CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1[C@@:25]([OH:40])([CH2:26][N:27]1[CH:31]=[N:30][CH:29]=[N:28]1)[C@H:32]([S:34][C@@H:35]1[CH2:36][O:37][C@@H:1]([C:3]2[CH:4]=[CH:5][C:6]([C:7]([NH:9][C:10]3[S:11][CH:12]=[CH:13][N:14]=3)=[O:8])=[CH:15][CH:16]=2)[O:2][CH2:38]1)[CH3:33]

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 149523114-formyl-N-(2-thiazolyl)benzamide

Product 1

HCID 178462407HCID 178462407, compoundYield 15%

Procedure

In the same manner as that described in Example 1(2), a reaction was carried out using 4-formyl-N-(2-thiazolyl)benzamide, obtained in Example 27(1) (200 mg, 0.86 mmol), (2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (270 mg, 0.75 mmol) and p-toluenesulfonic acid monohydrate (357 mg, 1.88 mmol) and the reaction mixture was treated using a similar procedure to that described in Example 1(2) to afford the trans isomer of the title compound (64 mg, yield 15%) as a white oil and the cis isomer (29 mg, yield 7%) as a colorless oil. The trans isomer was recrystallized from tetrahydrofuran-hexane to give white powdery crystals.

Workup

  1. additionthe reaction mixture was treated

Sources & evidence

ORD record
ord-c99f7163e8134e62b94800758d735bc1
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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