4-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl-amide] → 4-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid-(2,3,4-trihydroxy-butyl)-amide

HRID 654014Notes

Reaction equation

HRID 654014 reaction equation
[OH:1][CH:2]([CH:28]1[CH2:32][O:31]C(C)(C)[O:29]1)[CH2:3][NH:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:26])(=[O:25])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]([F:24])([F:23])[F:22])=[CH:8][CH:7]=1>CO.O>[OH:1][CH:2]([CH:28]([OH:29])[CH2:32][OH:31])[CH2:3][NH:4][C:5](=[O:27])[C:6]1[CH:11]=[CH:10][C:9]([S:12](=[O:25])(=[O:26])[NH:13][C:14]2[CH:19]=[CH:18][C:17]([F:20])=[CH:16][C:15]=2[C:21]([F:24])([F:22])[F:23])=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 150576084-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl-amide]

Product 1

HCID 150576094-[N-(4-Fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid-(2,3,4-trihydroxy-butyl)-amide

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

2.53 g (5 mmol) of 4-[N-(4-fluoro-2-trifluoromethylphenyl)sulfamoyl]-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide] is dissolved in 20 ml of methanol/water 1:1, about 100 mg of cation exchanger Amberlyst 15 is added and warmed for 1 hour to boiling temperature. The ion exchanger is then filtered off and the filtrate is evaporated to dryness in a vacuum. 1.74 g (3.75 mmol)=75% of the theoretical yield of the product is obtained as an amorphous solid.

Workup

  1. additionis added
  2. temperaturewarmed for 1 hour
  3. filtrationThe ion exchanger is then filtered off
  4. customthe filtrate is evaporated to dryness in a vacuum
  5. custom1.74 g (3.75 mmol)=75% of the theoretical yield of the product is obtained as an amorphous solid

Sources & evidence

ORD record
ord-4f5905b2d21a491c949312d317ca9b9e
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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