HCID 131723066, compound → HCID 131723067, compound

HRID 1249925Notes

Reaction equation

HRID 1249925 reaction equation
[F:1][C:2]([F:38])([F:37])[CH2:3][NH:4][C:5]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:16]CC3C=CC=CC=3)[CH:13]=2)[N:8]1[C:24](=[O:36])[C@@H:25]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH2:26][CH3:27])=[O:6].[H][H]>[Pd].C(OCC)(=O)C>[F:38][C:2]([F:1])([F:37])[CH2:3][NH:4][C:5]([CH:7]1[CH2:15][C:14]2[C:9](=[CH:10][CH:11]=[C:12]([OH:16])[CH:13]=2)[N:8]1[C:24](=[O:36])[C@@H:25]([NH:28][C:29]([O:31][C:32]([CH3:33])([CH3:35])[CH3:34])=[O:30])[CH2:26][CH3:27])=[O:6]

Participants

5

Reactant 2

HCID 131723066HCID 131723066, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 131723067HCID 131723067, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(N-t-butoxycarbonyl-2(S)-aminobutyryl)-5-benzyloxyindoline-2(R/S)-carboxylic acid 2,2,2-trifluoroethylamide (0.9 g, 1.68 mmol) and palladium on activated carbon (0.1 g, 10% wet) in ethyl acetate (20 mL) was hydrogenated under 30 psi hydrogen at room temperature overnight. Then the catalyst was removed by filtration over celite, and the filtrate was evaporated to provide a white solid.

Workup

  1. customThen the catalyst was removed by filtration over celite
  2. customthe filtrate was evaporated
  3. customto provide a white solid

Sources & evidence

ORD record
ord-e10cf40c24f2441f9b53f592c774287b
Source dataset
uspto-grants-2002_01
Patent number
US06335360B1

Reaction notes

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