Sodium Methoxide → HCID 86758339, compound

HRID 2228850Notes

Reaction equation

HRID 2228850 reaction equation
C[O-].[Na+].[CH2:4]([O:6][N:7]=[C:8]([CH2:28][C:29]([CH3:31])=[CH2:30])[C:9](=[C:11]([O:26][NH2:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][CH3:22])=[O:20])[CH3:10])[CH3:5]>CN(C=O)C>[CH2:4]([O:6][N:7]=[C:8]([CH:28]=[C:29]([CH3:30])[CH3:31])[C:9](=[C:11]([O:26][NH2:27])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](=[N:23][O:24][CH3:25])[C:19]([NH:21][CH3:22])=[O:20])[CH3:10])[CH3:5]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86758340HCID 86758340, compound

Product 1

HCID 86758339HCID 86758339, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
23 °C

Procedure

48.4 g of solid sodium methoxide in 400 ml of DMF were stirred at 23° C. for 3 hours, and 174 g of the amide from Example 8 in 250 ml of DMF were then added dropwise. The mixture was subsequently stirred at 23° C. for 18 hours and then worked-up similarly to Example 6. This gave 154 g of the title compound as a colorless solid which, according to NMR, GC and HPLC analysis, contained approximately 12% of the starting material (Example 8).

Sources & evidence

ORD record
ord-c91208a769af4f9ebcc15cc7eea78f27
Source dataset
uspto-grants-2002_07
Patent number
US06417388B1

Reaction notes

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