2-[3-methyl-2-(2-methylprop-1-en-1-yl)benzamido]-2,3-dihydro-1H-indene-2-carboxylic acid → 2-(2-Isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047777Notes

Reaction equation

HRID 1047777 reaction equation
[CH3:1][C:2]1[C:3]([CH:23]=[C:24]([CH3:26])[CH3:25])=[C:4]([CH:20]=[CH:21][CH:22]=1)[C:5]([NH:7][C:8]1([C:17]([OH:19])=[O:18])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=[O:6]>C(O)(=O)C.[Pd]>[CH2:23]([C:3]1[C:2]([CH3:1])=[CH:22][CH:21]=[CH:20][C:4]=1[C:5]([NH:7][C:8]1([C:17]([OH:19])=[O:18])[CH2:9][C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16]1)=[O:6])[CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 251606722-[3-methyl-2-(2-methylprop-1-en-1-yl)benzamido]-2,3-dihydro-1H-indene-2-carboxylic acid

Product 1

HCID 251606712-(2-Isobutyl-3-methyl-benzoylamino)-indan-2-carboxylic acidYield 54.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-[3-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid (135) (120 mg, 0.34 mmol) in acetic acid (15 mL) is added the catalyst, Pd—C (5 wt. % Pd, 72 mg, 3.4% mmol) under argon. The resulting reaction mixture is moved to the Paar apparatus to run hydrogenation: 50 psi, 95° C., overnight. The catalyst is removed by filtration through a pre-column (10 g silica gel) and washed by EtOH. The combined organic solution is concentrated in vacuo. The residue is purified by HPLC to give a pure product (136) as white solid (65 mg, 54%).

Workup

  1. customThe resulting reaction mixture
  2. custom50 psi, 95° C., overnight
  3. customThe catalyst is removed by filtration through a pre-column (10 g silica gel)
  4. washwashed by EtOH
  5. concentrationThe combined organic solution is concentrated in vacuo
  6. customThe residue is purified by HPLC

Sources & evidence

ORD record
ord-a2b8ab5e88fc4544afa7bcbf4b59923d
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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