p-Toluenesulfonic acid monohydrate → 3-[4-({[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid p-toluenesulfonate

HRID 508047Notes

Reaction equation

HRID 508047 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:24]([F:33])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:34])[CH:8]=1)[CH3:2].O.[C:36]1([CH3:46])[CH:41]=[CH:40][C:39]([S:42]([OH:45])(=[O:44])=[O:43])=[CH:38][CH:37]=1>C(OCC)C.C(OCC)(=O)C>[C:36]1([CH3:46])[CH:37]=[CH:38][C:39]([S:42]([OH:45])(=[O:43])=[O:44])=[CH:40][CH:41]=1.[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([CH2:20][NH:21][C:22]3[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][C:30]([OH:32])=[O:31])=[C:24]([F:33])[CH:23]=3)[CH:15]=2)=[C:9]([CH3:34])[CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 231572823-[4-({[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid

Product 1

HCID 866243753-[4-({[4'-(2-Ethoxyethoxy)-2',6'-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid p-toluenesulfonateYield 89.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 3-[4-({[4′-(2-ethoxyethoxy)-2′,6′-dimethylbiphenyl-3-yl]methyl}amino)-2-fluorophenyl]propanoic acid (0.372 g, 0.800 mmol) in diethyl ether (5 mL) was added a solution of p-toluenesulfonic acid monohydrate (0.152 g, 0.800 mmol) in ethyl acetate (5 mL), and the resulting crystals were washed with ethyl acetate-diethyl ether to give the title compound as colorless crystals (0.456 g, yield 89%).

Workup

  1. washthe resulting crystals were washed with ethyl acetate-diethyl ether

Sources & evidence

ORD record
ord-312b1c1d08144c79b741102394709e5d
Source dataset
uspto-grants-2010_08
Patent number
US07786165B2

Reaction notes

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