Methyl iodide → HCID 86725357, compound

HRID 925248Notes

Reaction equation

HRID 925248 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:10]2[C:11]3[CH:12]([OH:18])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].[H-].[Na+].I[CH3:24]>CN(C=O)C.O>[CH2:1]([O:3][C:4]([N:6]1[CH2:20][CH2:19][C:10]2[C:11]3[CH:12]([O:18][CH3:24])[CH2:13][CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86725356HCID 86725356, compound

Product 1

HCID 86725357HCID 86725357, compoundYield 112.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of the product from step (a) (45 mg, 0.16 mmol) in DMF (2 ml) at RT over an argon atmosphere was added NaH (16 mg, 0.41 mmol). The reaction mixture was stirred until gas evolution had ceased and then iodomethane (0.025 ml, 0.41 mmol) was added. The reaction mixture was stirred at RT for 24 hours. The reaction mixture was diluted with water and extracted with ethyl acetate (3×). The combined ethyl acetate extracts were washed with brine, dried (Na2SO4), and solvent evaporated in vacuo to give the sub-titled compound as a colorless oil (52 mg). MS: ESI (positive): 290 (M+H).

Workup

  1. stirringThe reaction mixture was stirred at RT for 24 hours
  2. extractionextracted with ethyl acetate (3×)
  3. washThe combined ethyl acetate extracts were washed with brine
  4. dry with materialdried (Na2SO4), and solvent
  5. customevaporated in vacuo

Sources & evidence

ORD record
ord-5a7480f78f254c67a443c6e5f6b6c3a2
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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