Ethanol → HCID 17928195, compound

HRID 1604662Notes

Reaction equation

HRID 1604662 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH2:18][C:19]1[CH:20]=[CH:21][C:22]3[O:26][C:25]([C:27]4[S:28][CH:29]=[C:30]([C:32]([CH3:35])([CH3:34])[CH3:33])[N:31]=4)=[CH:24][C:23]=3[CH:36]=1)[CH:13]=[C:12]2[CH2:37][C:38]([OH:40])=[O:39])C1C=CC=CC=1.[CH:41]([O-])=O.[NH4+].C(O)C>O>[C:32]([C:30]1[N:31]=[C:27]([C:25]2[O:26][C:22]3[CH:21]=[CH:20][C:19]([CH2:18][N:14]4[C:15]5[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=5)[C:12]([CH2:37][C:38]([O:40][CH3:41])=[O:39])=[CH:13]4)=[CH:36][C:23]=3[CH:24]=2)[S:28][CH:29]=1)([CH3:34])([CH3:35])[CH3:33]

Participants

5

Reactant 3

HCID 702EthanolHCID 2723923Ammonium formateHCID 19603740HCID 19603740, compound

Product 1

HCID 17928195HCID 17928195, compoundYield 68.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-benzyloxy-1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}indole-3-acetic acid (3.0 g), 10% Pd--C (0.6 g) and ammonium formate (2.0 g) in a mixed solvents of ethanol (60 ml) and water (6 ml) was stirred under reflux for 18 hours. After removal of the catalysts by filtration, the filtrate was concentrated under reduced pressure. The residue was dissolved in 10% hydrogen chloride in methanol (200 ml) and the mixture was stored in refrigerator for 2 days. The resulting solution was concentrated under reduced pressure and the residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and concentrated under reduced pressure to give methyl 1-{[2-(4-tert-butylthiazol-2-yl)benzofuran-5-yl]methyl}-5-hydroxyindole-3-acetate (1.76 g).

Workup

  1. temperatureunder reflux for 18 hours
  2. customAfter removal of the catalysts
  3. filtrationby filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. dissolutionThe residue was dissolved in 10% hydrogen chloride in methanol (200 ml)
  6. concentrationThe resulting solution was concentrated under reduced pressure
  7. customthe residue was partitioned between aqueous sodium hydrogen carbonate solution and ethyl acetate
  8. washThe organic layer was washed with brine
  9. dry with materialdried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-838d40c3e1aa462d97259f1fd7d999c7
Source dataset
uspto-grants-1999_11
Patent number
US05994378

Reaction notes

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