HCID 69804715, compound → HCID 69806845, compound

HRID 2414554Notes

Reaction equation

HRID 2414554 reaction equation
[CH3:1][O:2][C:3]([CH:5]1[CH2:11][N:10](CC2C=CC=CC=2)[CH2:9][CH2:8][CH2:7][N:6]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[O:4].[H][H]>C(O)C.[OH-].[OH-].[Pd+2]>[CH3:1][O:2][C:3]([CH:5]1[CH2:11][NH:10][CH2:9][CH2:8][CH2:7][N:6]1[S:19]([C:22]1[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=1)(=[O:21])=[O:20])=[O:4]

Participants

5

Reactant 2

HCID 69804715HCID 69804715, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 69806845HCID 69806845, compound

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 11.0 g (0.026 mol) of the product of Example 45 in 50 mL of ethanol was added 4.40 g of 20% palladium hydroxide on carbon (Pearlman's catalyst) and the resulting suspension was shaken at room temperature in a Parr reactor under 44 psi of hydrogen for 4 h. The reaction mixture was then filtered through Celite and the filter cake was washed with 100 mL of methanol. The filtrate was concentrated in vacuo and the residue was diluted with ethyl acetate. The solution was washed with water, dried over Na2SO4, filtered and concentrated in vacuo. The resulting oil was pure enough for use in the next step. Electrospray Mass Spec: 328.9 (M+H)+

Workup

  1. filtrationThe reaction mixture was then filtered through Celite
  2. washthe filter cake was washed with 100 mL of methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. additionthe residue was diluted with ethyl acetate
  5. washThe solution was washed with water
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-790c462941ec4569befaa76ae9858139
Source dataset
uspto-grants-2004_11
Patent number
US06812227B2

Reaction notes

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