HCID 14882639, compound → HCID 14882640, compound

HRID 330196Notes

Reaction equation

HRID 330196 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][C:14](=[O:20])[NH:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:10][CH:11]=2)[C:6]([CH2:21][C:22]2[CH:40]=[CH:39][C:25]([C:26]([NH:28][S:29]([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=3[CH3:38])(=[O:31])=[O:30])=[O:27])=[CH:24][C:23]=2[O:41][CH3:42])=[CH:5]1)[CH:2]=[CH2:3]>[OH-].[Na+].C(O)C.[Pd]>[CH2:16]([NH:15][C:14]([CH2:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[N:4]([CH2:1][CH2:2][CH3:3])[CH:5]=[C:6]2[CH2:21][C:22]1[CH:40]=[CH:39][C:25]([C:26]([NH:28][S:29]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=2[CH3:38])(=[O:31])=[O:30])=[O:27])=[CH:24][C:23]=1[O:41][CH3:42])=[O:20])[CH2:17][CH2:18][CH3:19]

Participants

5

Reactant 1

HCID 14882639HCID 14882639, compound

Product 1

HCID 14882640HCID 14882640, compoundYield 77%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4-[1-allyl-5-(butylcarbamoyl)methylindol-3-ylmethyl]-3-methoxy-N-(2-methylphenylsulfonyl)benzamide (0.35 g) in 1N sodium hydroxide (0.6 ml) and ethanol (10 ml) was hydrogenated at 3.45 bar in the presence of 10% (w/w) palladium-on-carbon (0.09 g) for 3 hours. The catalyst was removed by was evaporated. The residue was dissolved in H2O (10 ml) and the resultant aqueous solution was acidified with 10% (v/v) hydrochloric acid. The white precipitate which formed was collected by filtration, washed with water, and dried under vacuum to give the title compound (0.27 g, 77%) as a white powder; mp 100°-102°.

Workup

  1. customThe catalyst was removed
  2. customby was evaporated
  3. dissolutionThe residue was dissolved in H2O (10 ml)
  4. customThe white precipitate which formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-b96502b05af447e387215cd3b66d9cc6
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

Loading…