Methyl iodide → HCID 46841636, compound

HRID 2242589Notes

Reaction equation

HRID 2242589 reaction equation
[CH3:1][C:2]([C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][NH:29][C:30]([NH:32][CH2:33][CH3:34])=[O:31])[CH:23]=2)=[C:18]([OH:35])[CH:17]=1)([CH3:15])[CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:9]1[CH2:14][CH2:13][O:12][CH2:11][CH2:10]1)=[O:8].IC.[C:38]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:33]([NH:32][C:30]([NH:29][CH2:28][C:24]1[CH:23]=[C:22]([C:19]2[CH:20]=[CH:21][C:16]([C:2]([CH3:1])([CH2:3][CH2:4][CH2:5][CH2:6][C:7]([N:9]3[CH2:10][CH2:11][O:12][CH2:13][CH2:14]3)=[O:8])[CH3:15])=[CH:17][C:18]=2[O:35][CH3:38])[CH:27]=[CH:26][CH:25]=1)=[O:31])[CH3:34]

Participants

5

Reactant 3

HCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 11547510HCID 11547510, compound

Product 1

HCID 46841636HCID 46841636, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of 20 (0.1 g, 0.208 mmol, 1.0 eq), iodomethane (0.05 mL, 0.832 mmol, 4.0 eq), and K2CO3 (0.115 g, 0.832 mmol, 4.0 eq) in acetone (3 mL) was heated to 60° C. overnight. LC/MS showed SM/product ˜1/1. More K2CO3 (0.2 g, 1.45 mmol, 7 eq) and iodomethane (0.2 mL, 3.21 mmol, 15.4 eq) were added, and the mixture was heated again to 60° C. overnight. Acetone was removed under reduced pressure, and the residue was partitioned in water/ethyl acetate. The aqueous layer was extracted with ethyl acetate (2×20 mL), and the combined organic layer was washed by water (20 mL), brine (20 mL) and dried over anhydrous K2CO3. The solvent was removed under reduced pressure, and the residue was purified by column chromatography (silica gel, 60-100% ethyl acetate in hexane). Yield: 23%, 98% pure. M+1=496

Workup

  1. temperaturethe mixture was heated again to 60° C. overnight
  2. customAcetone was removed under reduced pressure
  3. customthe residue was partitioned in water/ethyl acetate
  4. extractionThe aqueous layer was extracted with ethyl acetate (2×20 mL)
  5. washthe combined organic layer was washed by water (20 mL), brine (20 mL)
  6. dry with materialdried over anhydrous K2CO3
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (silica gel, 60-100% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-8017699c55104e4a82c90d4afb97c871
Source dataset
uspto-grants-2010_03
Patent number
US07671052B2

Reaction notes

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