Sodium Hydroxide → HCID 24765489, compound

HRID 1255127Notes

Reaction equation

HRID 1255127 reaction equation
[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[C:15]1[S:19][C:18]([NH:20][C:21](=[O:30])[C:22]2[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=2[F:29])=[N:17][C:16]=1C(OC)=O)[CH:2]=[CH2:3].[OH-].[Na+]>CO>[CH2:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:12])[F:13])=[CH:7][C:6]=1[C:15]1[S:19][C:18]([NH:20][C:21](=[O:30])[C:22]2[C:23]([F:29])=[CH:24][CH:25]=[CH:26][C:27]=2[F:28])=[N:17][CH:16]=1)[CH:2]=[CH2:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 24765487HCID 24765487, compound

Product 1

HCID 24765489HCID 24765489, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Into a solution of Compound 63 (30 mg, 0.06 mmol) in 2 mL MeOH was added NaOH (50 mg). The solution was heated to reflux for 30 minutes. After cooling to room temperature, the solvent was removed, and the residue was dissolved in 4 mL of DMF and 1 mL of water. The mixture was heated to 150° C. for 16 hours. The mixture was diluted with 20 mL of Et2O and the solution was washed with brine, dried and concentrated. The residue was purified on silica (eluted with 10-50% of ethyl acetate in hexanes) to give Compound 65 (7.9 mg, 30%) as a white solid.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 30 minutes
  3. customthe solvent was removed
  4. dissolutionthe residue was dissolved in 4 mL of DMF
  5. temperatureThe mixture was heated to 150° C. for 16 hours
  6. additionThe mixture was diluted with 20 mL of Et2O
  7. washthe solution was washed with brine
  8. customdried
  9. concentrationconcentrated
  10. customThe residue was purified on silica (eluted with 10-50% of ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-1fa17b96ba184809a829b9a66702b8c2
Source dataset
uspto-grants-2013_06
Patent number
US08455658B2

Reaction notes

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