Water → 5-Fluoro-2-hydroxy-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid-(2,3,4-trihydroxybutyl)amide

HRID 654036Notes

Reaction equation

HRID 654036 reaction equation
FC1C=CC(S(=O)(=O)NC(F)(F)F)=CC=1C(O)=O.[OH:19][CH:20]([CH:48]1[CH2:52][O:51]C(C)(C)[O:49]1)[CH2:21][NH:22][C:23](=[O:47])[C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([C:31](=[O:38])[NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:25]=1[O:39]CC1C=CC=CC=1.O>CO.Cl.[C].[Pd]>[OH:19][CH:20]([CH:48]([OH:49])[CH2:52][OH:51])[CH2:21][NH:22][C:23](=[O:47])[C:24]1[CH:29]=[C:28]([F:30])[CH:27]=[C:26]([C:31](=[O:38])[NH:32][CH2:33][C:34]([F:37])([F:36])[F:35])[C:25]=1[OH:39]

Participants

7

Reactant 3

HCID 962WaterHCID 150576512-Benzyloxy-5-fluoro-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]HCID 19888158Fluoro-5 trifluoromethylsulfamoyl-benzoic acid

Product 1

HCID 150576525-Fluoro-2-hydroxy-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid-(2,3,4-trihydroxybutyl)amide

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

6.95 g (13.5 mmol) of 2 benzyloxy-5-fluoro-3-(2,2,2-trifluoroethylcarbamoyl)-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide] is dissolved in 20 ml of methanol, 5 ml of water and 5 ml of IN hydrochloric acid is added and stirred for 3 hours at room temperature. The solution is then adjusted to pH 6.3 by addition of anion exchanger Amberlite IRA 67, 200 mg of palladium-carbon (10%) is added and hydrogenated for 1 hour at normal pressure. The catalyst is then filtered off, the filtrate is evaporated to dryness in a vacuum and the residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol. 3.76 g (9.77 mmol)=72.4% of the theoretical yield of the compound is obtained as an amorphous solid.

Workup

  1. additionis added
  2. waithydrogenated for 1 hour at normal pressure
  3. filtrationThe catalyst is then filtered off
  4. customthe filtrate is evaporated to dryness in a vacuum
  5. customthe residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol
  6. custom3.76 g (9.77 mmol)=72.4% of the theoretical yield of the compound is obtained as an amorphous solid

Sources & evidence

ORD record
ord-58a2674689154518801ca19df28dcb16
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

Loading…