Methyl iodide → HCID 86612120, compound

HRID 2114855Notes

Reaction equation

HRID 2114855 reaction equation
CC[C@:3]1([CH3:19])[N:8]2[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([OH:12])=[C:7]2[C:6](=[O:18])[NH:5][CH2:4]1.C(N[C@H](C(O)=O)C)(O[C:23](C)(C)[CH3:24])=O.[C:33](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[CH2:23]([N:5]1[CH2:4][C@H:3]([CH3:19])[N:8]2[CH:9]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[C:11]([O:12][CH3:33])=[C:7]2[C:6]1=[O:18])[CH3:24]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 85082Tert-butoxycarbonylalanineHCID 69320966HCID 69320966, compound

Product 1

HCID 86612120HCID 86612120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of ethyl 4(S)-2-ethyl-8-hydroxy-4-methyl-1-oxo-1,2,3,4-tetrahydro-pyrrolo[1,2-a]-pyrazine-7-carboxylate (6.6 g, 25.8 mmol; prepared in a manner similar to the procedures described in Examples 32 and 45 starting with N-Boc-L-alanine) in DMF (125 mL), potassium carbonate (13.7 g, 99.1 mmol) and iodomethane (1.86 mL, 29.7 mmol) was added. The reaction mixture was stirred at rt over night. The mixture was filtered and the filtrate concentrated under vacuum. The residue was partitioned between dichloromethane and brine. The organic extract was washed with brine, dried over sodium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluted with ethyl acetate to give titled material.

Workup

  1. customprepared in a manner similar to the procedures
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate concentrated under vacuum
  4. customThe residue was partitioned between dichloromethane and brine
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. washeluted with ethyl acetate
  11. customto give titled material

Sources & evidence

ORD record
ord-d4ba471366114752872c4a062516390b
Source dataset
uspto-grants-2008_10
Patent number
US07435735B2

Reaction notes

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