Dimethylformamide → Methyl 4-(3,4-dihydro-4-methyl-3-oxo-1,4[2H]-benzothiazin-7-yl)-3-methyl-4-oxobutyrate

HRID 35185Notes

Reaction equation

HRID 35185 reaction equation
O=C1NC2[CH:8]=[CH:9][C:10]([C:12](=[O:19])[CH:13]([CH3:18])[CH2:14][C:15]([OH:17])=[O:16])=[CH:11][C:5]=2[S:4][CH2:3]1.[H-].[Na+].[CH3:22]I.[CH3:24][N:25]([CH3:28])[CH:26]=[O:27]>>[CH3:24][N:25]1[C:28]2[CH:8]=[CH:9][C:10]([C:12](=[O:19])[CH:13]([CH3:18])[CH2:14][C:15]([O:17][CH3:22])=[O:16])=[CH:11][C:5]=2[S:4][CH2:3][C:26]1=[O:27]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 150359234-(3,4-Dihydro-3-oxo-1,4[2H]-benzothiazin-7-yl)-3-methyl-4-oxobutyric acid

Product 1

HCID 15035924Methyl 4-(3,4-dihydro-4-methyl-3-oxo-1,4[2H]-benzothiazin-7-yl)-3-methyl-4-oxobutyrate

Procedure

4-(3,4-Dihydro-3-oxo-1,4[2H]-benzothiazin-7-yl)-3-methyl-4-oxobutyric acid (1.7 g) was dissolved in 50 ml of dimethylformamide and 0.23 g of 60% sodium hydride was added. After 30 minutes, 0.7 ml of methyl iodide was added and the mixture stirred at room temperature for three hours, then poured into 100 ml of ice water and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate and evaporated. The residue was chromatographed on a silica gel column eluted with 5% methanol in methylene chloride. The solvent was removed and the oil obtained was used in Example 56.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over sodium sulfate
  4. customevaporated
  5. customThe residue was chromatographed on a silica gel column
  6. washeluted with 5% methanol in methylene chloride
  7. customThe solvent was removed
  8. customthe oil obtained

Sources & evidence

ORD record
ord-4797ccf44dd24bf5aafbf1ec1ac8b6b6
Source dataset
uspto-grants-1988_08
Patent number
US04766118

Reaction notes

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