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

HRID 654052Notes

Reaction equation

HRID 654052 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])=[C:16]([C:21]([F:24])([F:23])[F:22])[CH:15]=2)=[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])=[C:16]([C:21]([F:24])([F:22])[F:23])[CH:15]=2)=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 678993514-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]

Product 1

HCID 198881734-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl]-benzoic acid-(2,3,4-trihydroxybutyl)amide

Reagents, catalysts & solvents 1

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

Procedure

Analogously to Example 1l(b), 3.8 g (7.5 mmol) of 4-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide] in methanol/water with cation exchanger is converted into the title compound. 1.74 g=83% of the theoretical yield is obtained as an amorphous solid.

Sources & evidence

ORD record
ord-dddff2b45d004d33866b330fe0003f13
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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