Sodium Methoxide → HCID 11362125, compound

HRID 985158Notes

Reaction equation

HRID 985158 reaction equation
[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH2:9][N:10]([CH2:29][C:30]#[N:31])[C:11]([C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:14]=1[C:21]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)=O)=[O:12])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+]>CO>[C:1]([O:5][C:6](=[O:32])[NH:7][CH2:8][CH2:9][N:10]1[C:29]([C:30]#[N:31])=[C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:14]2[C:13](=[CH:18][CH:17]=[C:16]([O:19][CH3:20])[CH:15]=2)[C:11]1=[O:12])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 20768295HCID 20768295, compound

Product 1

HCID 11362125HCID 11362125, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 112 (3.16 g, 7.23 mmol), sodium methoxide (0.5M, 31.8 mL, 15.9 mmol) and methanol (100 mL) was heated at reflux for 1 h. The solvent was removed in vacuo and sat. sodium bicarbonate was added. Extracted with methylene chloride (3×). The combined organic extracts were dried with magnesium sulfate (anh.) and filtered. The filtrate was removed in vacuo to give 113 as a white solid (3.04 g, 7.23 mmol, 100%).

Workup

  1. temperatureat reflux for 1 h
  2. customThe solvent was removed in vacuo and sat. sodium bicarbonate
  3. additionwas added
  4. extractionExtracted with methylene chloride (3×)
  5. dry with materialThe combined organic extracts were dried with magnesium sulfate (anh.)
  6. filtrationfiltered
  7. customThe filtrate was removed in vacuo

Sources & evidence

ORD record
ord-4101e43c8159440a8df69005da30d729
Source dataset
uspto-grants-2005_03
Patent number
US06870055B2

Reaction notes

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