Sodium Methoxide → HCID 21029358, compound

HRID 1828755Notes

Reaction equation

HRID 1828755 reaction equation
C[O-].[Na+].[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C:15](=[O:17])[CH:14]=[CH:13][N:12]2C(O[C@@H]2C[C@H](C)CC[C@H]2C(C)C)=O)=[C:7]([CH3:31])[CH:6]=1>CO>[F:4][C:5]1[CH:10]=[CH:9][C:8]([C@H:11]2[CH2:16][C:15](=[O:17])[CH:14]=[CH:13][NH:12]2)=[C:7]([CH3:31])[CH:6]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86598850HCID 86598850, compound

Product 1

HCID 21029358HCID 21029358, compoundYield 161%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (100 mg) was added to a solution of intermediate 6b (170 mg) in MeOH (15 mL) under a nitrogen atmosphere. The mixture was refluxed for two hours, and the solvent was removed in vacuo. The residue was partitioned between water (10 mL) and AcOEt (15 mL). The layers were separated, and the aqueous phase was extracted with further AcOEt (4×10 mL). The combined organic extracts were washed with brine (10 mL), dried and concentrated in vacuo to give the title compound (145 mg) as a light yellow oil.

Workup

  1. temperatureThe mixture was refluxed for two hours
  2. customthe solvent was removed in vacuo
  3. customThe residue was partitioned between water (10 mL) and AcOEt (15 mL)
  4. customThe layers were separated
  5. extractionthe aqueous phase was extracted with further AcOEt (4×10 mL)
  6. washThe combined organic extracts were washed with brine (10 mL)
  7. customdried
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2cfc4f6475244ec9b3e1f9948bb2af16
Source dataset
uspto-grants-2006_06
Patent number
US07060702B2

Reaction notes

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