2-[4-Benzyloxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester → 2-[4-Hydroxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl ester

HRID 1810920Notes

Reaction equation

HRID 1810920 reaction equation
[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:40])[C:16]2[CH:21]=[CH:20][C:19]([O:22]CC3C=CC=CC=3)=[C:18]([O:30][CH2:31][CH2:32][C:33]3[CH:34]=[C:35]([CH3:39])[CH:36]=[CH:37][CH:38]=3)[CH:17]=2)[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH2:6]1)=[O:4].[H][H]>CC(=O)OCC.[Pd]>[CH3:1][O:2][C:3]([C:5]1([NH:14][C:15](=[O:40])[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:30][CH2:31][CH2:32][C:33]3[CH:34]=[C:35]([CH3:39])[CH:36]=[CH:37][CH:38]=3)[CH:17]=2)[CH2:6][C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH2:13]1)=[O:4]

Participants

5

Reactant 2

HCID 670767132-[4-Benzyloxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 670762682-[4-Hydroxy-3-(2-m-tolyl-ethoxy)-benzoylamino]-indane-2-carboxylic acid methyl esterYield 45.2%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 23938PalladiumSolvent

Procedure

The compound of step 3 of example 253 (800 mg, 1.49 mmol) was dissolved in EA (15 ml) and hydrogenated in the presence of palladium (10%) on charcoal (200 mg) at a hydrogen pressure of 5 bar and room temperature for 6 h. The mixture was filtered over silica gel and evaporated to dryness. The residue was purified by RP HPLC (water/ACN gradient) to yield 300 mg of the title compound.

Workup

  1. filtrationThe mixture was filtered over silica gel
  2. customevaporated to dryness
  3. customThe residue was purified by RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-aea47fbbc8c84e8c8cb351e80d81b674
Source dataset
uspto-grants-2013_01
Patent number
US08362073B2

Reaction notes

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