Water → HCID 15057661, compound

HRID 654041Notes

Reaction equation

HRID 654041 reaction equation
[OH:1][CH:2]([CH:19]1[CH2:23][O:22]C(C)(C)[O:20]1)[CH2:3][NH:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([C:13]([F:16])([F:15])[F:14])[C:7]=1[OH:17].O>CO>[OH:1][CH:2]([CH:19]([OH:20])[CH2:23][OH:22])[CH2:3][NH:4][C:5](=[O:18])[C:6]1[CH:11]=[C:10]([F:12])[CH:9]=[C:8]([C:13]([F:15])([F:16])[F:14])[C:7]=1[OH:17]

Participants

4

Reactant 2

HCID 962WaterHCID 67899874HCID 67899874, compound

Product 1

HCID 15057661HCID 15057661, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

6.86 g (15 mmol) of 5-fluoro-2-hydroxy-3-(trifluoromethyl)-benzoic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide] is dissolved in 30 ml of methanol, 30 ml of water and 300 mg of cation exchanger Amberlyst 15 are added and refluxed for 2 hours. The ion exchanger is then filtered off, 250 mg of palladium-carbon (10%) is added to the filtrate 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. 3.08 mg (9.41 mmol)=62.7% of the theoretical yield of the compound is obtained as an amorphous solid.

Workup

  1. temperaturerefluxed for 2 hours
  2. filtrationThe ion exchanger is then filtered off
  3. addition250 mg of palladium-carbon (10%) is added to the filtrate and hydrogenated for 1 hour at normal pressure
  4. filtrationThe catalyst is then filtered off
  5. customthe filtrate is evaporated to dryness in a vacuum
  6. customthe residue is chromatographed on silica gel 60 (Merck) with dichloromethane/methanol
  7. custom3.08 mg (9.41 mmol)=62.7% of the theoretical yield of the compound is obtained as an amorphous solid

Sources & evidence

ORD record
ord-56743e1916884a2990195c13711476ff
Source dataset
uspto-grants-1992_07
Patent number
US05130119

Reaction notes

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