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 2405273Notes

Reaction equation

HRID 2405273 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-23b026db79eb4a3bb81860fd5709b250
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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