Water → Edaglitazone

HRID 2306036Notes

Reaction equation

HRID 2306036 reaction equation
[Al].O.[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][CH2:16][O:17][C:18]1[C:26]2[CH:25]=[CH:24][S:23][C:22]=2[C:21]([CH:27]=[C:28]2[S:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])=[CH:20][CH:19]=1>O1CCCC1>[CH3:3][C:4]1[O:8][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[N:6][C:5]=1[CH2:15][CH2:16][O:17][C:18]1[C:26]2[CH:25]=[CH:24][S:23][C:22]=2[C:21]([CH2:27][CH:28]2[S:32][C:31](=[O:33])[NH:30][C:29]2=[O:34])=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 962WaterHCID 5359268AluminumHCID 853192475-[[4-[2-(5-Methyl-2-phenyl-4-oxazolyl)ethoxy]-benzo[b]thien-7-yl]methylene]-2,4-thiazolidinedione

Product 1

HCID 9825701Edaglitazone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

10 g activated aluminium needles and 1 ml water are added to a solution of 2.03 g (4.3 mmol) 5-{4-[2-(5-Methyl-2-phenyloxazol-4-yl)-ethoxy]-benzo[b]thiophen-7-ylmethylidene}-thiazolidine-2,4-dione (Fp. 204-207° C.) in 130 ml tetrahydrofuran. Then it is heated for 50 min. while stirring to 50° C. and the solid components are removed by filtration. The filtrate is evaporated and the residue is chromatographed on silica gel with a mixture of 88 parts by volume toluene, 10 parts by volume 2-butanone and 2 parts by volume glacial acetic acid.

Workup

  1. temperatureThen it is heated for 50 min.
  2. customthe solid components are removed by filtration
  3. customThe filtrate is evaporated
  4. customthe residue is chromatographed on silica gel with a mixture of 88 parts by volume toluene, 10 parts by volume 2-butanone and 2 parts by volume glacial acetic acid

Sources & evidence

ORD record
ord-e069d3a071974f489ffc03e7f9f68061
Source dataset
uspto-grants-2002_08
Patent number
US06441185B2

Reaction notes

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