HCID 87629799, compound → HCID 68936891, compound

HRID 2095280Notes

Reaction equation

HRID 2095280 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:13]2[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:35]=[CH:34][C:33](OS(C(F)(F)F)(=O)=O)=[C:32]2[C:27]=1[CH:28]1[CH2:44][CH:31]2[CH2:30][CH2:29]1.[H][H]>O1CCCC1.CO.[OH-].[Pd+2].[OH-]>[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:16]=1[NH:15][C:14]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[C:13]2[CH2:22][CH2:23][CH2:24][O:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH:28]1[CH2:44][CH:31]2[CH2:30][CH2:29]1

Participants

6

Reactant 2

HCID 87629799HCID 87629799, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 68936891HCID 68936891, compound

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of EXAMPLE 546D (80 mg) in tetrahydrofuran and methanol (40 ml, 1:1) was added 10% palladium hydroxide (40 mg). The mixture was shaken under 30 psi of hydrogen for 4 hours. The catalyst was filtered off, the filtrate was concentrated and the residue was hydrolyzed with LiOH/tetrahydrofuran/methanol/H2O. The product was purified by reverse phase HPLC.

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe product was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-0d6de1100e8b4c7e822bf3d7a4b571a3
Source dataset
uspto-grants-2013_05
Patent number
US08445679B2

Reaction notes

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