Methyl iodide → HCID 66862381, compound

HRID 253000Notes

Reaction equation

HRID 253000 reaction equation
C[O-].[Na+].[C:4](=O)([S:6][CH2:7][C@@H:8]1[CH2:12][CH2:11][CH2:10][N:9]1[C:13](=[O:21])[C:14]1[CH:19]=[CH:18][C:17]([Br:20])=[CH:16][CH:15]=1)C.CI.C(=O)([O-])O.[Na+]>CO>[Br:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]([N:9]2[CH2:10][CH2:11][CH2:12][C@H:8]2[CH2:7][S:6][CH3:4])=[O:21])=[CH:15][CH:16]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 516892Sodium BicarbonateHCID 10942334Sodium MethoxideHCID 86631209HCID 86631209, compound

Product 1

HCID 66862381HCID 66862381, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Sodium methoxide (0.22 ml, 0.876 mmol) (28% in methanol) was added to a solution of 100 mg (0.292 mmol) of the title compound produced in step (iv) of Reference Example 8 in methanol (1 ml), and the mixture was stirred at room temperature for 15 min. Thereafter, 0.11 ml (1.75 mmol) of methyl iodide was added thereto, and the mixture was stirred at room temperature for 20 hr. The reaction was stopped by adding a saturated aqueous sodium hydrogencarbonate solution, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated brine in that order, was dried over anhydrous sodium sulfate, and was then filtered. The filtrate was concentrated under the reduced pressure, and the residue was purified by preparative thin layer chromatography (hexane:ethyl acetate=1:4) to give 55 mg (yield 60%) of the title compound.

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. extractionthe reaction solution was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine in that order
  4. dry with materialwas dried over anhydrous sodium sulfate
  5. filtrationwas then filtered
  6. concentrationThe filtrate was concentrated under the reduced pressure
  7. customthe residue was purified by preparative thin layer chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-aca6f3acfcab4d4aac07a64259deb71d
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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