2-[N-(2,4,6-Trifluorophenyl)sulfamoyl]-acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide] → 2-[N-(2,4,6-trifluorophenyl)sulfamoyl]-acetic acid-[2,3,4-trihydroxy-butylamide]

HRID 654009Notes

Reaction equation

HRID 654009 reaction equation
[OH:1][CH:2]([CH:21]1[CH2:25][O:24]C(C)(C)[O:22]1)[CH2:3][NH:4][C:5](=[O:20])[CH2:6][S:7](=[O:19])(=[O:18])[NH:8][C:9]1[C:14]([F:15])=[CH:13][C:12]([F:16])=[CH:11][C:10]=1[F:17]>CO.O>[OH:1][CH:2]([CH:21]([OH:22])[CH2:25][OH:24])[CH2:3][NH:4][C:5](=[O:20])[CH2:6][S:7](=[O:18])(=[O:19])[NH:8][C:9]1[C:10]([F:17])=[CH:11][C:12]([F:16])=[CH:13][C:14]=1[F:15]

Participants

4

Reactant 1

HCID 150576032-[N-(2,4,6-Trifluorophenyl)sulfamoyl]-acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]

Product 1

HCID 678252672-[N-(2,4,6-trifluorophenyl)sulfamoyl]-acetic acid-[2,3,4-trihydroxy-butylamide]

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

2.22 g (6 mmol) of 2-[N-(2,4,6-trifluorophenyl)sulfamoyl]-acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethyl-amide] is dissolved in a mixture of 10 ml of methanol and 5 ml of water, about 100 mg of cation exchanger Amberlyst 15 is added and it is warmed to boiling temperature in 1 hour. The ion exchanger is then filtered off and the filtrate is evaporated to dryness in a vacuum. 1.94 g (5.24 mmol) =87.3% of the theoretical yield of the product is obtained as an amorphous solid.

Workup

  1. additionis added
  2. temperatureit is warmed
  3. customin 1 hour
  4. filtrationThe ion exchanger is then filtered off
  5. customthe filtrate is evaporated to dryness in a vacuum
  6. custom1.94 g (5.24 mmol) =87.3% of the theoretical yield of the product is obtained as an amorphous solid

Sources & evidence

ORD record
ord-3f4c72f5eaa4483c855695dcbf2ca698
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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