2-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid → 2-(2-Isobutyl-4-methyl-benzoylamino)-indan-2-carboxylic acid

HRID 1047891Notes

Reaction equation

HRID 1047891 reaction equation
[CH3:1][C:2]1[CH:22]=[CH:21][C:5]([C:6]([NH:8][C:9]2([C:18]([OH:20])=[O:19])[CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH2:10]2)=[O:7])=[C:4]([CH:23]=[C:24]([CH3:26])[CH3:25])[CH:3]=1>C(O)(=O)C.[Pd]>[CH2:23]([C:4]1[CH:3]=[C:2]([CH3:1])[CH:22]=[CH:21][C:5]=1[C:6]([NH:8][C:9]1([C:18]([OH:20])=[O:19])[CH2:10][C:11]2[C:16](=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:17]1)=[O:7])[CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 1

HCID 593143752-[4-Methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid

Product 1

HCID 593141202-(2-Isobutyl-4-methyl-benzoylamino)-indan-2-carboxylic acidYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 2-[4-methyl-2-(2-methyl-propenyl)-benzoylamino]-indan-2-carboxylic acid (510 mg, 1.45 mmol) in glacial acetic acid (65 mL) under N2 is added Pd/C (10% Pd, 138 mg, 10 mol %). The reaction is hydrogenated at 60 psi H2 and 90° C. overnight. The reaction is cooled to RT and filtered through Celite, washing the filter cake with water (2×15 mL) and MeOH (2×15 mL); the filtrate is concentrated in vacuo. The residue is dissolved in water (75 mL) and extracted with EtOAc (2×30 mL). The combined organic layers are washed with a 5% NaHCO3 solution (3×20 mL), water (20 mL) and brine (20 mL) then dried over anhydrous Na2SO4. The organic layer is concentrated in vacuo to give product (280) as white solid (350 mg, 69%).

Workup

  1. customis hydrogenated at 60 psi H2 and 90° C. overnight
  2. filtrationfiltered through Celite
  3. washwashing the filter cake with water (2×15 mL) and MeOH (2×15 mL)
  4. concentrationthe filtrate is concentrated in vacuo
  5. dissolutionThe residue is dissolved in water (75 mL)
  6. extractionextracted with EtOAc (2×30 mL)
  7. washThe combined organic layers are washed with a 5% NaHCO3 solution (3×20 mL), water (20 mL) and brine (20 mL)
  8. dry with materialthen dried over anhydrous Na2SO4
  9. concentrationThe organic layer is concentrated in vacuo

Sources & evidence

ORD record
ord-a8576cabb31344ba8df303c0345d9e06
Source dataset
uspto-grants-2013_10
Patent number
US08569535B2

Reaction notes

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