Methyl iodide → HCID 67130488, compound

HRID 1746596Notes

Reaction equation

HRID 1746596 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([OH:24])=[O:23])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][CH3:21])[CH:12]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:25](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[C:1]([O:5][C:6]([NH:8][C@H:9]([C:22]([O:24][CH3:25])=[O:23])[CH2:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]([CH2:20][CH3:21])[CH:12]=1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 54148847HCID 54148847, compound

Product 1

HCID 67130488HCID 67130488, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To DMF (80 mL) solution of the compound obtained in Example 137 (5,7 g) was added potassium carbonate (3.6 g) and iodomethane (1.6 mL) at 0° C., and the mixture was stirred for 17 hours at room temperature. The reaction mixture was poured into ice water, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and thereafter the residue obtained by distilling off the solvent under a reduced pressure was purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1), to give the captioned compound (4.8 g, 81%) as an oily product.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe residue obtained
  4. distillationby distilling off the solvent under a reduced pressure
  5. customwas purified with silica gel column chromatography (n-hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-2c62662da1da40f488c70057dbabc0c9
Source dataset
uspto-grants-2015_10
Patent number
US09150510B2

Reaction notes

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