HCID 18926524, compound → HCID 18926516, compound

HRID 1600193Notes

Reaction equation

HRID 1600193 reaction equation
C(OC([NH:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:18]([CH3:29])=[C:17]2[CH2:30][N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1)=O)C1C=CC=CC=1>O1CCCC1.[Pd]>[NH2:11][CH2:12][CH2:13][C:14]1[CH:15]=[C:16]2[C:20](=[CH:21][CH:22]=1)[N:19]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:18]([CH3:29])=[C:17]2[CH2:30][N:31]1[CH:35]=[CH:34][N:33]=[CH:32]1

Participants

4

Reactant 1

HCID 18926524HCID 18926524, compound

Product 1

HCID 18926516HCID 18926516, compoundYield 79.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 5-(2-benzyloxycarbonylaminoethyl)-3-(1H-imidazol-1-ylmethyl)-2-methyl-1H-indole-1-propanoate (0.57 g) in tetrahydrofuran (50 ml) was hydrogenated at room temperature and 4.5 atm. pressure in the presence 10% palladium on carbon (50 mg) for 20 hours. The mixture was filtered and the residue was washed with methanol. The filtrate and washings were combined and evaporated to give a gum which was chromatographed on silica gel. Elution with dichloromethane/methanol (19:1) gave impurity, and then further elution with dichloromethane/methanol/0.880 ammonia solution (95:5:1) gavepure product. The product fractions were evaporated to give the title compound as a gum (0.325 g), Rf. 0.4 (SS3). The product was used directly for further reaction.

Workup

  1. customwas hydrogenated at room temperature
  2. filtrationThe mixture was filtered
  3. washthe residue was washed with methanol
  4. customevaporated
  5. customto give a gum which
  6. customwas chromatographed on silica gel
  7. washElution with dichloromethane/methanol (19:1)
  8. customgave impurity
  9. washfurther elution with dichloromethane/methanol/0.880 ammonia solution (95:5:1) gavepure product
  10. customThe product fractions were evaporated

Sources & evidence

ORD record
ord-6ae8654dde6441dca0b0fa487a544a8a
Source dataset
uspto-grants-1998_04
Patent number
US05744488

Reaction notes

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