2-[2-((E)-2-cyclopropyl-vinyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid → 2-[2-(2-Cyclopropyl-ethyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

HRID 1047780Notes

Reaction equation

HRID 1047780 reaction equation
[CH:1]1(/[CH:4]=[CH:5]/[C:6]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=2[C:8]([NH:10][C:11]2([C:20]([OH:22])=[O:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:9])[CH2:3][CH2:2]1>CCO.[Pd]>[CH:1]1([CH2:4][CH2:5][C:6]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:7]=2[C:8]([NH:10][C:11]2([C:20]([OH:22])=[O:21])[CH2:19][C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[CH2:12]2)=[O:9])[CH2:2][CH2:3]1

Participants

4

Reactant 1

HCID 251607962-[2-((E)-2-cyclopropyl-vinyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid

Product 1

HCID 251607972-[2-(2-Cyclopropyl-ethyl)-3-methyl-benzoylamino]-indan-2-carboxylic acidYield 25%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 2-[2-((E)-2-cyclopropyl-vinyl)-3-methyl-benzoylamino]-indan-2-carboxylic acid (138) (120 mg, 0.33 mmol) in absolute EtOH (10 mL) is added the catalyst, Pd—C (5 wt. % Pd, 28 mg, 1.3% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, room temperature, overnight. The catalyst is removed by the filtration through a pre-column (10 g silica gel) and washed by EtOH. The combined solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (139) as white solid (30 mg, 25%).

Workup

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

Sources & evidence

ORD record
ord-44df93285864436d99c798cca29d06f1
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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