HCID 59253985, compound → HCID 59253940, compound

HRID 2169749Notes

Reaction equation

HRID 2169749 reaction equation
[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:19]CC2C=CC=CC=2)=[CH:8][CH:7]=1>CO.CN(C)C=O.[Pd]>[CH3:1][O:2][C:3](=[O:28])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=[CH:8][CH:7]=1

Participants

5

Reactant 1

HCID 59253985HCID 59253985, compound

Product 1

HCID 59253940HCID 59253940, compoundYield 24.4%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

4-(6-Benzyloxyhexanoylamino)phenoxyacetic acid methyl ester 76 (24 grams, 62.33 mmol) was dissolved in a mixture of methanol (200 ml) and dimethylformamide (50 ml) in a pressure vessel, palladium on carbon (5%, 15 g) was added and the mixture stirred under a hydrogen atm. (4 Kg) for 24 hrs. Catalyst was removed by filtration, and the solvents were distilled off under vacuum. Crude 77 was purified by column chromatography on silica gel using chloroform as eluant to get pure 77 (4.5 g, 24.4%) as a white powder. M.p: 87.5-90.4° C.

Workup

  1. customCatalyst was removed by filtration
  2. distillationthe solvents were distilled off under vacuum
  3. customCrude 77 was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-bfc3c7ef45344a1bb7212f3be7a8f41a
Source dataset
uspto-grants-2015_06
Patent number
USRE045548E1

Reaction notes

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