p-Toluenesulfonic acid monohydrate → 4'-(2-[(1S,2R)-2-Hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylic acid p-toluenesulfonate

HRID 30778Notes

Reaction equation

HRID 30778 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH:13][C@H:14]([C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=1)[C@@H:15]([NH:17][CH2:18][CH2:19][O:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([OH:36])=[O:35])=[CH:30][CH:29]=2)=[CH:23][C:22]=1[CH3:37])[CH3:16]>O1CCOCC1.C(OCC)C>[C:2]1([CH3:12])[CH:3]=[CH:4][C:5]([S:8]([OH:11])(=[O:9])=[O:10])=[CH:6][CH:7]=1.[OH:13][C@H:14]([C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[CH:40][CH:39]=1)[C@@H:15]([NH:17][CH2:18][CH2:19][O:20][C:21]1[C:26]([CH3:27])=[CH:25][C:24]([C:28]2[CH:33]=[CH:32][C:31]([C:34]([OH:36])=[O:35])=[CH:30][CH:29]=2)=[CH:23][C:22]=1[CH3:37])[CH3:16]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 68540748HCID 68540748, compound2×

Product 1

HCID 866055124'-(2-[(1S,2R)-2-Hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy)-3',5'-dimethylbiphenyl-4-carboxylic acid p-toluenesulfonateYield 45%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

p-Toluenesulfonic acid monohydrate (0.042 g) was added to a suspension of 4′-{2-[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethylamino]ethoxy}-3′,5′-dimethylbiphenyl-4-carboxylic acid (compound 1, 0.094 g) in 1,4-dioxane (1.1 mL), and the mixture was stirred at room temperature for 1 hr. The clear solution was diluted with an excess amount of diethyl ether, and the precipitate was collected by filtration to afford the title compound (0.059 g) as a white amorphous. The structure and physical data were shown in table 4.

Workup

  1. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4285992760fd442ebbeea5579c678004
Source dataset
uspto-grants-2008_09
Patent number
US07423185B2

Reaction notes

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