alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanol → 2-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl] acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]

HRID 654049Notes

Reaction equation

HRID 654049 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])=[CH:4][C:3]=1[C:16]([F:19])([F:18])[F:17].[OH:20][CH:21]([CH:24]1[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]1)[CH2:22][NH2:23]>O1CCOCC1>[OH:20][CH:21]([CH:24]1[CH2:28][O:27][C:26]([CH3:30])([CH3:29])[O:25]1)[CH2:22][NH:23][C:13](=[O:15])[CH2:12][S:9](=[O:10])(=[O:11])[NH:8][C:5]1[CH:6]=[CH:7][C:2]([F:1])=[C:3]([C:16]([F:19])([F:18])[F:17])[CH:4]=1

Participants

4

Reactant 2

HCID 11971028alpha-(Aminomethyl)-2,2-dimethyl-1,3-dioxolane-4-methanolHCID 197640082-[N-(4-fluoro-3-trifluoromethylphenyl)sulfamoyl]acetic acid

Product 1

HCID 678996912-[N-(4-Fluoro-3-trifluoromethylphenyl)sulfamoyl] acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Analogously to the instructions for Example 9(a), 2.21 g (7 mmol) of 2-[N-(4-fluoro-3-trifluoromethyl-phenyl)sulfamoyl] acetic acid in dioxane is reacted with 1.13 g (7 mmol) of 2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamine for about 1 hour at 90° C. After concentration by evaporation and crystallization from ethanol/ether, 2.87 g=92.3% of the theoretical yield is obtained as a crystallizate. Melting point 144°-146° C.

Workup

  1. concentrationAfter concentration
  2. customby evaporation and crystallization from ethanol/ether, 2.87 g=92.3% of the
  3. customtheoretical yield
  4. customis obtained as a crystallizate

Sources & evidence

ORD record
ord-d5f814d27334473d87ebcdc33b9e8a41
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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