Methyl iodide → HCID 58067201, compound

HRID 406922Notes

Reaction equation

HRID 406922 reaction equation
[CH3:1][O:2][CH:3]([O:23][CH3:24])[CH2:4][N:5]1[CH:10]=[CH:9][C:8](=[O:11])[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]1[C:20]([OH:22])=[O:21].[C:25]([O-])(O)=O.[Na+].CI>CN(C=O)C.CC(OC)(C)C.CCOC(C)=O>[CH3:24][O:23][CH:3]([O:2][CH3:1])[CH2:4][N:5]1[CH:10]=[CH:9][C:8](=[O:11])[C:7]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:6]1[C:20]([O:22][CH3:25])=[O:21]

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 46239167HCID 46239167, compound

Product 1

HCID 58067201HCID 58067201, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

Crude 1-[2,2-bis(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylic acid 22 obtained as above was dissolved in DMF (500 mL). To this solution was added NaHCO3 (50.5 g, 0.6 mole). The suspension was stirred vigorously with a mechanic stirrer while CH3I in TBME (2.0 M, 300 mL) was introduced by addition funnel over 30 minutes. After addition, the reaction was stirred overnight at room temperature. The reaction mixture was then diluted with EtOAc (˜1.5 L) and washed with water and brine. The organic layer was dried over anhydrous Na2SO4. Evaporation of solvents gave methyl 1-[2,2-bis(methyloxy)ethyl]-4-oxo-3-[(phenylmethyl)oxy]-1,4-dihydro-2-pyridinecarboxylate 23 as brown oil, which was used directly for the next step.

Workup

  1. additionwas introduced by addition funnel over 30 minutes
  2. additionAfter addition
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous Na2SO4
  5. customEvaporation of solvents

Sources & evidence

ORD record
ord-756b558050264ed791ab8c2f69eaf6c8
Source dataset
uspto-grants-2014_06
Patent number
US08754214B2

Reaction notes

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