Sodium Methoxide → HCID 14659592, compound

HRID 1440197Notes

Reaction equation

HRID 1440197 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[N:7]([C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:6]1)(=O)C.C[O-].[Na+]>CO>[CH2:27]([O:26][C:24]([N:7]1[C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@@H:5]([OH:4])[CH2:6]1)=[O:25])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 15930594HCID 15930594, compound

Product 1

HCID 14659592HCID 14659592, compoundYield 85.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Compound (2) (9.13 g) was dissolved in methanol (100 ml). To this solution, sodium methoxide was added at 0° C. until the pH became almost 12, followed by stirring at 0° C. for 1 hour. After completion of the reaction, the solution was neutralized with ion exchange resin Amberlite IR-120 (H+). The resin was filtered out and washed with methanol. The filtrate was combined with washings, followed by concentration under reduced pressure. The resulting residue was subjected to column chromatography (Wako Gel C-200, dichloromethane/methanol=50/1 ) to yield compound (3) (4.96 g, 85.1%).

Workup

  1. customAfter completion of the reaction
  2. filtrationThe resin was filtered out
  3. washwashed with methanol
  4. concentrationfollowed by concentration under reduced pressure

Sources & evidence

ORD record
ord-b4a29309e3f94b578e3fcaab0268364b
Source dataset
uspto-grants-1996_03
Patent number
US05498604

Reaction notes

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