(s,s)-5-(5-Fluoro-2,3-dihydro-indol-1-yl)-4-[4-methyl-2-(3-methyl-benzoylamino)-pentanoylamino]-pentanoic acid benzyl ester → (s,s)-5-(5-Fluoro-2,3-dihydro-indol-1-yl)-4-[4-methyl-2-(3-methyl-benzoylamino)-pentanoylamino]-pentanoic acid

HRID 132138Notes

Reaction equation

HRID 132138 reaction equation
C([O:8][C:9](=[O:42])[CH2:10][CH2:11][C@H:12]([NH:24][C:25](=[O:41])[C@@H:26]([NH:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=1)[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:13][N:14]1[C:22]2[C:17](=[CH:18][C:19]([F:23])=[CH:20][CH:21]=2)[CH2:16][CH2:15]1)C1C=CC=CC=1.[H][H]>[Pd].CO>[F:23][C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[N:14]([CH2:13][C@@H:12]([NH:24][C:25](=[O:41])[C@@H:26]([NH:31][C:32](=[O:40])[C:33]1[CH:38]=[CH:37][CH:36]=[C:35]([CH3:39])[CH:34]=1)[CH2:27][CH:28]([CH3:30])[CH3:29])[CH2:11][CH2:10][C:9]([OH:42])=[O:8])[CH2:15][CH2:16]2

Participants

5

Reactant 2

HCID 11192417(s,s)-5-(5-Fluoro-2,3-dihydro-indol-1-yl)-4-[4-methyl-2-(3-methyl-benzoylamino)-pentanoylamino]-pentanoic acid benzyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 11386148(s,s)-5-(5-Fluoro-2,3-dihydro-indol-1-yl)-4-[4-methyl-2-(3-methyl-benzoylamino)-pentanoylamino]-pentanoic acid

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The title compound of Example 42 (200 mg, 0.348 mmol) and 10% Pd/C were treated with MeOH (2 mL) and the atmosphere in the reaction was switched to hydrogen. After stirring overnight, the atmosphere in the reaction was switched back to nitrogen and the reaction was filtered through celite. Removal of solvent and drying afforded a white solid (168 mg, 94); HPLC-MS calcd. for C27H34FN3O4 (M+H+) 484.3, found 484.4.

Workup

  1. filtrationthe reaction was filtered through celite
  2. customRemoval of solvent
  3. customdrying
  4. customafforded a white solid (168 mg, 94)

Sources & evidence

ORD record
ord-75daac9e37ae4b838e748bac9087390b
Source dataset
uspto-grants-2008_06
Patent number
US07384970B2

Reaction notes

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