p-Toluenesulfonic acid monohydrate → HCID 178462409, compound
Reaction equation
[C:1]([C:3]1[CH:20]=[CH:19][C:6]([CH2:7][NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([CH:16]=[O:17])=[CH:12][CH:11]=2)=[CH:5][CH:4]=1)#[N:2].[F:21][C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[C@:29]([OH:44])([C@H:36]([S:38][CH:39]([CH2:42]O)[CH2:40][OH:41])[CH3:37])[CH2:30][N:31]1[CH:35]=[N:34][CH:33]=[N:32]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][NH:8][C:9](=[O:18])[C:10]2[CH:15]=[CH:14][C:13]([C@H:16]3[O:41][CH2:40][C@H:39]([S:38][C@H:36]([CH3:37])[C@:29]([C:23]4[CH:24]=[CH:25][C:26]([F:28])=[CH:27][C:22]=4[F:21])([OH:44])[CH2:30][N:31]4[CH:35]=[N:34][CH:33]=[N:32]4)[CH2:42][O:17]3)=[CH:12][CH:11]=2)=[CH:19][CH:20]=1)#[N:2]Participants
Procedure
In the same manner as that described in Example 1(2), a reaction was carried out using N-(4-cyanobenzyl)-4-formylbenzamide, obtained in Example 26(1) (200 mg, 0.76 mmol), (2R,3R)-2-(2,4-difluorophenyl)-3-[[1-(hydroxymethyl)-2-hydroxyethyl]thio]-1-(1H-1,2,4-triazol-1-yl)-2-butanol (237 mg, 0.66 mmol) and p-toluenesulfonic acid monohydrate (151 mg, 0.79 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 (137 mg, yield 34%) as a white solid and the cis isomer (82 mg, yield 21%) as a white solid. The trans isomer was recrystallized from tetrahydrofuran-hexane to give white powdery crystals and the cis isomer was recrystallized from ethyl acetate to give white powdery cryatals.
Workup
- additionthe reaction mixture was treated
Sources & evidence
- ORD record
- ord-542411bdd91e436bb3463befd3d2faa2
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06653330B2
Reaction notes
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