HCID 86659595, compound → HCID 86659596, compound

HRID 451320Notes

Reaction equation

HRID 451320 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([C@@H:17]2[CH2:23][CH2:22][C@@H:21]3[CH2:24][N:18]2[C:19](=[O:33])[N:20]3[O:25]CC2C=CC=CC=2)=[O:16])[C@H:10]([F:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.C(OCC)(=O)C.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]([C@@H:17]2[CH2:23][CH2:22][C@@H:21]3[CH2:24][N:18]2[C:19](=[O:33])[N:20]3[OH:25])=[O:16])[C@H:10]([F:34])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 86659595HCID 86659595, compound

Product 1

HCID 86659596HCID 86659596, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of the product of Step 1 (3.0175 g, 6.33 mmol) in methanol (80 mL) and ethyl acetate (20 mL), was added 10% palladium on carbon (0.73 g, 6.86 mmol) and the reaction mixture was stirred under an atmosphere of hydrogen (balloon) overnight. LC/MS analysis showed reaction was complete. The reaction mixture was filtered through a microfilter and the collected solid was washed well with methanol. The filtrate was concentrated under vacuum and azeotroped with toluene to afford the title compound as a yellow foam which was used directly in the next step without purification

Workup

  1. customreaction
  2. filtrationThe reaction mixture was filtered through a microfilter
  3. washthe collected solid was washed well with methanol
  4. concentrationThe filtrate was concentrated under vacuum
  5. customazeotroped with toluene

Sources & evidence

ORD record
ord-24300814fffa4c94aff515c271239bda
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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