HCID 20186756, compound → HCID 20186772, compound

HRID 2309010Notes

Reaction equation

HRID 2309010 reaction equation
[NH2:1][C:2]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:15][CH2:16][CH:17]([C:22]2[CH:27]=[CH:26][C:25]([O:28]CC3C=CC=CC=3)=[CH:24][CH:23]=2)[O:18][CH2:19][CH2:20][OH:21])[CH3:14])=[CH:8][CH:7]=1)=[O:3].[H][H]>C(O)(=O)C.[Pd]>[NH2:1][C:2]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH:13]([NH:15][CH2:16][CH:17]([O:18][CH2:19][CH2:20][OH:21])[C:22]2[CH:23]=[CH:24][C:25]([OH:28])=[CH:26][CH:27]=2)[CH3:14])=[CH:8][CH:7]=1)=[O:3]

Participants

5

Reactant 2

HCID 20186756HCID 20186756, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 20186772HCID 20186772, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

N-[2-(4-Aminocarbonylmethoxyphenyl)-1-methylethyl]-2-(4-benzyloxyphenyl)-2-(2-hydroxyethoxy)ethanamine (3.5 g) in glacial acetic acid (30 ml) was hydrogenated in the presence of 10% Palladium on carbon at atmospheric pressure and room temperature until hydrogen uptake was complete. The solution was filtered through diatomaceous earth and the solvent removed under vacuum. The residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate, the organic layer separated, dried (MgSO4) and evaporated to give an oil. The oil was crystallised from ethyl acetate to give the title compound, m.p. 145°-160° C. as a 40:60 mixture of diastereoisomers.

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. customthe solvent removed under vacuum
  3. customThe residue was partitioned between ethyl acetate and saturated aqueous sodium bicarbonate
  4. customthe organic layer separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto give an oil
  8. customThe oil was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-a64b69f23e884ed786d7306f6684c519
Source dataset
uspto-grants-1987_09
Patent number
US04692465

Reaction notes

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