2-[2-(-1-Ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid → 2-[2-(1-Ethyl-butyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

HRID 1047771Notes

Reaction equation

HRID 1047771 reaction equation
[CH2:1]([C:3]([C:7]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:8]=1[C:9]([NH:11][C:12]1([C:21]([OH:23])=[O:22])[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)=[O:10])=[CH:4][CH2:5][CH3:6])[CH3:2]>CCO.[Pd]>[CH2:1]([CH:3]([C:7]1[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:8]=1[C:9]([NH:11][C:12]1([C:21]([OH:23])=[O:22])[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[CH2:13]1)=[O:10])[CH2:4][CH2:5][CH3:6])[CH3:2]

Participants

4

Reactant 1

HCID 685896612-[2-(-1-Ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

Product 1

HCID 251604122-[2-(1-Ethyl-butyl)-3-methyl-benzoylamino]-indan-2-carboxylic acidYield 28%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[2-(-1-ethyl-but-1-enyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid ethyl ester (129) (270 mg, 0.72 mmol) in absolute EtOH (15 mL) is added the catalyst, Pd—C (50% wetted powder, 10% Pd, 46 mg, 2.2% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, 70° C., overnight. The catalyst is removed by the filtration through a pre-column (10 g silica gel) and washed by EtOH. The combined EtOH solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (130) as white solid (75 mg, 28%).

Workup

  1. customThe resulting reaction mixture
  2. custom50 psi, 70° C., overnight
  3. customThe catalyst is removed by the filtration through a pre-column (10 g silica gel)
  4. washwashed by EtOH
  5. concentrationThe combined EtOH solution is concentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-782c1c68e126403bace2e5a06958cf06
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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