p-Toluenesulfonic acid monohydrate → HCID 178461714, compound

HRID 480941Notes

Reaction equation

HRID 480941 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@@:28]([OH:43])([CH2:37][N:38]1[CH:42]=[N:41][CH:40]=[N:39]1)[C@@H:29]([CH3:36])[CH2:30][CH:31]([CH2:34]O)[CH2:32][OH:33].O.C1(C)C=CC(S(O)(=O)=O)=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:33][CH2:32][C@H:31]([CH2:30][C@H:29]([CH3:36])[C@:28]([C:22]4[CH:23]=[CH:24][C:25]([F:27])=[CH:26][C:21]=4[F:20])([OH:43])[CH2:37][N:38]4[CH:42]=[N:41][CH:40]=[N:39]4)[CH2:34][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 69832629HCID 69832629, compound

Product 1

HCID 178461714HCID 178461714, compoundYield 60.1%

Procedure

In the same manner as described in Example 1(2), a reaction was carried out using 4′-cyano-4-formylbenzanilide (78 mg, 0.31 mmol) obtained in Example 2(1), (4S,5R)-5-(2,4-difluorophenyl)-2-(hydroxymethyl)-4-methyl-6-(1H-1,2,4-triazol-1-yl)-1,5-hexanediol (disclosed in Japanese Patent Application Publication No. Hei-11-80135: 100 mg, 0.29 mmol) and p-toluenesulfonic acid monohydrate (99 mg, 0.52 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 (100 mg, yield 59%) as a white solid and the cis isomer (23 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-30875e40efa24d0b8204ed08b76bb36d
Source dataset
uspto-grants-2003_11
Patent number
US06653330B2

Reaction notes

Loading…