HCID 90384405, compound → HCID 90384301, compound

HRID 928651Notes

Reaction equation

HRID 928651 reaction equation
[F:1][C:2]1[C:7]2[CH:8]=[CH:9][O:10][C:6]=2[C:5]([C:11]2[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:4][C:3]=1[F:18].[H][H]>C(O)(=O)C.[C].[Pd]>[F:1][C:2]1[C:7]2[CH2:8][CH2:9][O:10][C:6]=2[C:5]([C:11]2[CH:12]=[CH:13][C:14]([OH:17])=[CH:15][CH:16]=2)=[CH:4][C:3]=1[F:18]

Participants

5

Reactant 2

HCID 90384405HCID 90384405, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 90384301HCID 90384301, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 176Acetic AcidSolvent

Procedure

The compound (568 mg, 2.31 mmol) of Step 1 was dissolved in acetic acid (25 mL), and a catalytic amount of 10% palladium-carbon was added thereto, and stirred in a hydrogen atmosphere of 4 atm overnight. The insoluble material was filtered off, and the solvent was distilled away under reduced pressure. The resulting residue was purified by reversed-phase HPLC in the same manner as in Step 2 of Example 1 to thus obtain the title compound.

Workup

  1. filtrationThe insoluble material was filtered off
  2. distillationthe solvent was distilled away under reduced pressure
  3. customThe resulting residue was purified by reversed-phase HPLC in the same manner as in Step 2 of Example 1

Sources & evidence

ORD record
ord-b88a5ae2a04b47698c75af1a935092c5
Source dataset
uspto-grants-2016_03
Patent number
US09290487B2

Reaction notes

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