Sodium Methoxide → HCID 58745501, compound

HRID 723481Notes

Reaction equation

HRID 723481 reaction equation
[C:1]1([C@@H:7]([NH:9][C@H:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][C@H:11]2[C:23]([O:25][CH3:26])=[O:24])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O-].[Na+]>CO>[C:1]1([C@@H:7]([NH:9][C@H:10]2[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:12][C@@H:11]2[C:23]([O:25][CH3:26])=[O:24])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 58745527HCID 58745527, compound

Product 1

HCID 58745501HCID 58745501, compoundYield 33.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 258A (4.50 g, 12.4 mmol) in methanol (124 mL) at room temperature was treated with 25% NaOMe in methanol (8.04 mL). This reaction mixture was heated to 50° C. for 3.0 hours, cooled to room temperature, and then concentrated in vacuo. The oily residue was dissolved in dichloromethane (200 mL), and washed with 20% NH4Cl (2×75 mL). The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash chromatography (10 to 25% EtOAc/hexanes) on silica gel to give 1.50 g (yield: 30%) of Compound 260A as an oil.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe oily residue was dissolved in dichloromethane (200 mL)
  4. washwashed with 20% NH4Cl (2×75 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography (10 to 25% EtOAc/hexanes) on silica gel

Sources & evidence

ORD record
ord-528612845b594428a1a4ebfbd6761c25
Source dataset
uspto-grants-2006_11
Patent number
US07141571B2

Reaction notes

Loading…