p-Toluenesulfonic acid monohydrate → HCID 178462396, compound

HRID 480936Notes

Reaction equation

HRID 480936 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][C:6]([NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([CH:15]=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2].[F:20][C:21]1[CH:26]=[C:25]([F:27])[CH:24]=[CH:23][C:22]=1[C@@H:28]([C@H:36]([S:38][CH:39]([CH2:42][OH:43])[CH2:40]O)[CH3:37])[CH:29]([N:31]1[CH:35]=[N:34][CH:33]=[N:32]1)O.O.C1(C)C=CC(S(O)(=O)=[O:52])=CC=1>>[C:1]([C:3]1[CH:19]=[CH:18][C:6]([NH:7][C:8](=[O:17])[C:9]2[CH:14]=[CH:13][C:12]([C@H:15]3[O:43][CH2:42][C@H:39]([S:38][C@H:36]([CH3:37])[C@:28]([C:22]4[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=4[F:20])([OH:52])[CH2:29][N:31]4[CH:35]=[N:34][CH:33]=[N:32]4)[CH2:40][O:16]3)=[CH:11][CH:10]=2)=[CH:5][CH:4]=1)#[N:2]

Participants

4

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 18766367N-(4-Cyanophenyl)-4-formylbenzamideHCID 69832989HCID 69832989, compound

Product 1

HCID 178462396HCID 178462396, compoundYield 19%

Procedure

In the same manner as that described in Example 1(2), a reaction was carried out using 4′-cyano-4-formylbenzanilide (75 mg, 0.30 mmol) obtained in Example 2(1), (2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)butanol (98 mg, 0.27 mmol) and p-toluenesulfonic acid monohydrate (62 mg, 0.32 mmol) and the reaction mixture was treated using a similar procedure to that described in Example 1(2) to give the trans isomer of the title compound (30 mg, yield 19%) as a white solid and the cis isomer (20 mg, yield 12%) as a white solid. 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-4f1b302a582a41a2ab5546dee86bc072
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

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