HCID 57048090, compound → HCID 57203581, compound

HRID 1164999Notes

Reaction equation

HRID 1164999 reaction equation
[OH:1][CH:2]([CH2:17][NH:18][CH2:19][CH2:20][NH:21][C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[CH2:3][O:4][C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10].[H][H]>CO.[Pd]>[OH:1][CH:2]([CH2:17][NH:18][CH2:19][CH2:20][NH:21][C:22](=[O:26])[CH2:23][CH2:24][CH3:25])[CH2:3][O:4][C:5]1[CH:16]=[CH:15][CH:14]=[CH:13][C:6]=1[CH2:7][CH2:8][C:9]([O:11][CH3:12])=[O:10]

Participants

5

Reactant 2

HCID 57048090HCID 57048090, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 57203581HCID 57203581, compoundYield 85.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 3.0 g (0.008 mole) of methyl 2-[2-hydroxy-3-[N-[2-(methylpropionamido)ethyl]amino]propoxy]cinnamate in 100 ml of methanol was treated with 0.3 g of 10% Pd-C catalyst and hydrogenated at 40 psi until no further uptake of hydrogen was observed (about 48 hr.). The catalyst was removed by filtration and the filtrate concentrated under reduced pressure to a solid, which was recrystallized from methanol:ether to provide 2.5 g (83%) of product, having a melting point of 119°-120° C. The IR and NMR spectra and elemental analysis were consistent with the assigned structure.

Workup

  1. custom(about 48 hr.)
  2. customThe catalyst was removed by filtration
  3. concentrationthe filtrate concentrated under reduced pressure to a solid, which
  4. customwas recrystallized from methanol

Sources & evidence

ORD record
ord-aa26ab98a3284897831f4a5524684d35
Source dataset
uspto-grants-1990_03
Patent number
US04906661

Reaction notes

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