HCID 54569424, compound → HCID 54047362, compound

HRID 1609757Notes

Reaction equation

HRID 1609757 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[NH:9][C:10](=[O:25])[C:11]1[CH:16]=[CH:15][C:14]([O:17]CC2C=CC=CC=2)=[CH:13][CH:12]=1>C(O)C.[Pd]>[CH3:1][O:2][C:3](=[O:26])[C@@H:4]1[CH2:8][CH2:7][CH2:6][N:5]1[NH:9][C:10](=[O:25])[C:11]1[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 54569424HCID 54569424, compound

Product 1

HCID 54047362HCID 54047362, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The above amide (10.0 g, 29.4 mmol) dissolved in 75 mL of absolute ethanol. To this solution was added 3 g of 10% Pd/C. The mixture was hydrogenated at 1 atm for 5 hours The catalyst was then removed by passing the reaction through a pad of celite. Concentration of the filtrate provided crude N-(4-hydroxybenzamido)-L-proline methyl ester that was purified by chromatography (SiO2, 30% ethyl acetate/hexanes) to provide 6.3 g (86%) as a white solid. MS.

Workup

  1. customThe catalyst was then removed
  2. customthe reaction through a pad of celite

Sources & evidence

ORD record
ord-4d5002cb7540439981e49f4a9460293b
Source dataset
uspto-grants-1995_03
Patent number
US05401851

Reaction notes

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