Sodium Hydroxide → HCID 68830561, compound

HRID 734740Notes

Reaction equation

HRID 734740 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]1[C:17]([O:19]C)=[O:18].[OH-].[Na+]>CO>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:9]1[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]1[C:17]([OH:19])=[O:18]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 68829653HCID 68829653, compound

Product 1

HCID 68830561HCID 68830561, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

The product from Step 1 (600 mg, 2.13 mmol) was dissolved in methanol (15 mL), NaOH solution (5 mL, 2.5 M) was added, and this reaction mixture was heated to 60° C. for 18 h. The reaction mixture was concentrated, and then poured into EtOAc (20 mL) and water (5 mL). The aqueous layer was acidified to pH<3 with 6N HCl, and extracted with EtOAc (50 mL). The organic phase was washed with brine, dried over Na2SO4, filtered and concentrated. The residue was triturated with 5% ether/hexanes to afford the title compound (312 mg, 55%). MS (ES+) m/e 268 [M+H]+.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionpoured into EtOAc (20 mL) and water (5 mL)
  3. extractionextracted with EtOAc (50 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was triturated with 5% ether/hexanes

Sources & evidence

ORD record
ord-52378dc7332944d6a70270602545e727
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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