Methyl iodide → HCID 86614980, compound

HRID 2378547Notes

Reaction equation

HRID 2378547 reaction equation
[CH:1]1([O:6][C:7]2[C:12]([NH:13][C:14](=[O:19])[C:15]([F:18])([F:17])[F:16])=[CH:11][C:10]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:9][C:8]=2[C:26]2[CH:35]=[CH:34][C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:27]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].CI.[C:40](OCC)(=O)C>CN(C=O)C>[CH:1]1([O:6][C:7]2[C:8]([C:26]3[CH:35]=[CH:34][C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[CH:27]=3)=[CH:9][C:10]([CH2:20][CH2:21][C:22]([O:24][CH3:25])=[O:23])=[CH:11][C:12]=2[N:13]([CH3:40])[C:14](=[O:19])[C:15]([F:17])([F:16])[F:18])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 86614981HCID 86614981, compound

Product 1

HCID 86614980HCID 86614980, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of Intermediate 54 (208 mg) in DMF (5 ml) was added with 60% sodium hydride (21 mg) under ice cooling, and stirred for 20 minutes. This reaction mixture was added dropwise with methyl iodide (150 μl), stirred for 10 minutes, then warmed to room temperature, and further stirred for 1 hour. The reaction mixture was poured into ice water, and ethyl acetate (100 ml) was added for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Quad, hexane:ethyl acetate 5:1) to obtain the title compound (Intermediate 55, 200 mg).

Workup

  1. stirringstirred for 10 minutes
  2. stirringfurther stirred for 1 hour
  3. additionwas added for extraction
  4. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  5. customdried
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by column chromatography (Quad, hexane:ethyl acetate 5:1)

Sources & evidence

ORD record
ord-ea2b3a44b3664204b606c144a52c7f55
Source dataset
uspto-grants-2008_12
Patent number
US07470807B2

Reaction notes

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