Sodium Methoxide → HCID 21029358, compound

HRID 1178313Notes

Reaction equation

HRID 1178313 reaction equation
C[O-].[Na+].C([C@@H]1CC[C@@H](C)C[C@H]1OC([N:17]1[CH:22]=[CH:21][C:20](=[O:23])[CH2:19][CH:18]1[C:24]1[CH:29]=[CH:28][C:27]([F:30])=[CH:26][C:25]=1[CH3:31])=O)(C)C>CO>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C@H:18]2[CH2:19][C:20](=[O:23])[CH:21]=[CH:22][NH:17]2)=[C:25]([CH3:31])[CH:26]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86760555HCID 86760555, 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-d177576c2a9643fc877db5c03f7b4030
Source dataset
uspto-grants-2007_10
Patent number
US07276509B2

Reaction notes

Loading…