1-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2-(methylamino)ethan-1-ol → 3-Fluoro-6-(trifluoromethylsulfamoyl)-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl-N-methyl-amide]

HRID 654055Notes

Reaction equation

HRID 654055 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]([S:11](=[O:18])(=[O:17])[NH:12][C:13]([F:16])([F:15])[F:14])=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[CH3:19][NH:20][CH2:21][CH:22]([CH:24]1[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]1)[OH:23]>>[OH:23][CH:22]([CH:24]1[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]1)[CH2:21][N:20]([CH3:19])[C:5](=[O:7])[C:4]1[C:8]([S:11](=[O:18])(=[O:17])[NH:12][C:13]([F:16])([F:15])[F:14])=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=1

Participants

3

Reactant 2

HCID 150576531-(2,2-Dimethyl-1,3-dioxolan-4-yl)-2-(methylamino)ethan-1-olHCID 198881613-Fluoro-6-(trifluoromethylsulfamoyl)-benzoic acid

Product 1

HCID 678998663-Fluoro-6-(trifluoromethylsulfamoyl)-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl-N-methyl-amide]

Procedure

Analogously to Example 22(a), 4.31 g (15 mmol) of 3-fluoro-6-(trifluoromethylsulfamoyl)-benzoic acid is reacted with 3.22 g (20 mmol) of 2-methylamino-1-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethanol and the crude product is purified by chromatography on silica gel with ethyl acetate/hexane. 4.93 g=76.3% of the theoretical yield is obtained as an amorphous solid.

Workup

  1. customthe crude product is purified by chromatography on silica gel with ethyl acetate/hexane
  2. custom4.93 g=76.3% of the theoretical yield
  3. customis obtained as an amorphous solid

Sources & evidence

ORD record
ord-57012b63f9d4471da44824f3e8e36838
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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