2-[3-(Hydroxy-o-tolyl-methyl)-4-methoxy-benzoylamino]-indane-2-carboxylic acid → 2-[4-Methoxy-3-(2-methyl-benzyl)-benzoylamino]-indane-2-carboxylic acid

HRID 521505Notes

Reaction equation

HRID 521505 reaction equation
O[CH:2]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32])[C:3]1[CH:4]=[C:5]([CH:21]=[CH:22][C:23]=1[O:24][CH3:25])[C:6]([NH:8][C:9]1([C:18]([OH:20])=[O:19])[CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:10]1)=[O:7].[H][H]>C(O)C.[Pd]>[CH3:25][O:24][C:23]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])=[CH:4][C:3]=1[CH2:2][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[CH3:32]

Participants

5

Reactant 2

HCID 670765032-[3-(Hydroxy-o-tolyl-methyl)-4-methoxy-benzoylamino]-indane-2-carboxylic acidHCID 178418361HCID 178418361, compound

Product 1

HCID 670766382-[4-Methoxy-3-(2-methyl-benzyl)-benzoylamino]-indane-2-carboxylic acidYield 81.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The compound of example 241 (32 mg, 0.074 mmol) was dissolved in ethanol (10 ml), palladium (10%) on charcoal (10 mg) was added, and the mixture was hydrogenated at room temperature for 1 h at a hydrogen pressure of 5 bar. After completion of the reaction, the mixture was filtered over silica gel and evaporated to dryness. The residue was triturated with diethyl ether, filtered and dried in vacuo to yield 25 mg of the title compound.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe mixture was filtered over silica gel
  3. customevaporated to dryness
  4. customThe residue was triturated with diethyl ether
  5. filtrationfiltered
  6. customdried in vacuo

Sources & evidence

ORD record
ord-df4751416a7341b08d11b6bdd3e0f995
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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