2-[2-(3-Methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid → 2-[2-(3-Methoxy-propyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

HRID 1047843Notes

Reaction equation

HRID 1047843 reaction equation
[CH3:1][O:2][CH2:3][CH:4]=[CH:5][C:6]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=1[C:8]([NH:10][C:11]1([C:20]([OH:22])=[O:21])[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH2:12]1)=[O:9]>CCO.[Pd]>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][C:6]1[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=1[C:8]([NH:10][C:11]1([C:20]([OH:22])=[O:21])[CH2:12][C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:19]1)=[O:9]

Participants

4

Reactant 1

HCID 685908492-[2-(3-Methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

Product 1

HCID 593143722-[2-(3-Methoxy-propyl)-3-methyl-benzoylamino]-indan-2-carboxylic acidYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[2-(3-methoxy-propenyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid (229) (120 mg, 0.34 mmol) in absolute EtOH (15 mL) is added the catalyst, Pd—C (5 wt. % Pd, 93 mg, 4.4% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 55 psi, 50° C., overnight. The catalyst is removed by the filtration through a pre-column (10 g silica gel) and washed with EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (222) as white solid (80 mg, 49%).

Workup

  1. customThe resulting reaction mixture
  2. custom55 psi, 50° C., overnight
  3. customThe catalyst is removed by the filtration through a pre-column (10 g silica gel)
  4. washwashed with EtOH
  5. concentrationThe combined organic solution is concentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-0851da02b73e41c5ad5dc18327297e84
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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