Ethyl Acetate → HCID 58975006, compound

HRID 737020Notes

Reaction equation

HRID 737020 reaction equation
[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([C:22]3[CH2:26][CH2:25][CH2:24][CH:23]=3)=[CH:14]2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.C(OCC)(=O)C.[H][H]>[Pd].C(O)C>[CH3:1][O:2][C:3](=[O:27])[C:4]1[CH:9]=[CH:8][C:7]([S:10]([N:13]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]([CH:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)=[CH:14]2)(=[O:11])=[O:12])=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 589750154-(3-Cyclopent-1-enyl-indole-1-sulfonyl)-benzoic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 58975006HCID 58975006, compoundYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 3 gallon autoclave, charge 4-(3-Cyclopent-1-enyl-indole-1-sulfonyl)-benzoic acid methyl ester (475 g), ethyl acetate (2.5 L), absolute ethanol (2.5 L) and 10% Pd—C (45 g, w/w) under 35 psi hydrogen at ambient temperature for 5 hours. Filter the crude reaction over Hyflo. Concentrate the filtrate under vacuum to give a light yellow solid (465 g) of the title compound.

Workup

  1. filtrationFilter the crude
  2. customreaction over Hyflo
  3. concentrationConcentrate the filtrate under vacuum

Sources & evidence

ORD record
ord-a34fe5ebc83e45108e0e7a6c5961cbcd
Source dataset
uspto-grants-2009_09
Patent number
US07595339B2

Reaction notes

Loading…