Taurine → 2-[2-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]acetylamino]ethanesulfonic Acid

HRID 248746

Reaction equation

HRID 248746 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][C:13]([OH:15])=O)(=[O:11])=[O:10])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1.[NH2:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24].O.OC1C2N=NNC=2C=CC=1.C(N(CC)CC)C.C1(N=C=NC2CCCCC2)CCCCC1>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][S:9]([CH2:12][C:13]([NH:20][CH2:21][CH2:22][S:23]([OH:26])(=[O:25])=[O:24])=[O:15])(=[O:10])=[O:11])=[C:4]([C:16]([F:19])([F:18])[F:17])[CH:3]=1

Participants

7

Reactant 5

HCID 1123TaurineHCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 156765552-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acidHCID 178526939HCID 178526939, compound

Product 1

HCID 197640222-[2-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]acetylamino]ethanesulfonic Acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under the conditions of Example 2(a), 3.012 g (10 mmol) of 2-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]acetic acid, 1.252 g (10 mmol) of 2aminoethanesulfonic acid, 1.531 g (10 mmol) of hydroxybenzotriazole, hydrate, as well as 1.012 g (10 mmol) of triethylamine and 2.063 g (10 mmol) of dicyclohexylcarbodiimide are reacted and worked up analogously. The crude product is dissolved in distilled water, extracted with ethyl acetate, and converted into the free acid by treatment with acidic cation exchanger. The title compound is obtained by freeze-drying the aqueous solution.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-2d8c875dee1d4a2eaae5ac95928e4f7c
Source dataset
uspto-grants-1993_05
Patent number
US05210290

Linked notes

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