Sodium Hydroxide → HCID 25254605, compound

HRID 333810Notes

Reaction equation

HRID 333810 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH:5]([C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])[C:6]([OH:18])([C:11]1[CH:16]=[N:15][CH:14]=[C:13]([CH3:17])[N:12]=1)[C:7]([F:10])([F:9])[F:8].[OH-].[Na+]>CO>[Cl:26][C:20]1[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=1[CH:5]([C:6]([OH:18])([C:11]1[CH:16]=[N:15][CH:14]=[C:13]([CH3:17])[N:12]=1)[C:7]([F:9])([F:8])[F:10])[CH2:4][C:3]([OH:27])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 25254604HCID 25254604, compound

Product 1

HCID 25254605HCID 25254605, compoundYield 73.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

3-(2,4-Dichloro-phenyl)-5,5,5-trifluoro-4-hydroxy-4-(6-methyl-pyrazin-2-yl)-pentanoic acid methyl ester (Example 117, 42 mg) was dissolved in MeOH (1 mL), treated with a 1N NaOH aqueous solution (0.2 ml) and stirred at 40° C. for 5 h. The MeOH was evaporated in vacuo and a 1N HCl aqueous solution (0.2 ml) was added. The resulting suspension was extracted twice with ethyl acetate. The combined organic layer were washed with water and brine, dried over magnesium sulfate and evaporated. The residue was purified by flash chromatography (silica gel, ethyl acetate in heptane 2:1) to give the title compound as a colorless semisolid (30 mg). MS (m/e)=409.3 (MH+).

Workup

  1. customThe MeOH was evaporated in vacuo
  2. additiona 1N HCl aqueous solution (0.2 ml) was added
  3. extractionThe resulting suspension was extracted twice with ethyl acetate
  4. washThe combined organic layer were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by flash chromatography (silica gel, ethyl acetate in heptane 2:1)

Sources & evidence

ORD record
ord-114e86966fff4eaf983c3025e0b79e96
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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