Methyl iodide → HCID 57847045, compound

HRID 550292Notes

Reaction equation

HRID 550292 reaction equation
[H-].[Na+].[OH:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH:26][C:27](=[O:34])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1.CI.[C:37](=O)([O-])O.[Na+]>O1CCCC1>[CH3:37][O:3][CH2:4][C@H:5]1[C@H:14]2[CH2:15][CH2:16][N:17]([C:18]([C@H:20]3[CH2:25][CH2:24][CH2:23][CH2:22][C@H:21]3[NH:26][C:27](=[O:34])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[O:19])[C@H:13]2[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[NH:6]1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 57847141HCID 57847141, compound

Product 1

HCID 57847045HCID 57847045, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in oil, 14 mg, 0.1 mmol) was suspended in tetrahydrofuran (1 ml), the compound (35 mg, 0.08 mmol) synthesized in Example 50 was added under ice-cooling, and the suspension was stirred for 1 hr. Methyl iodide (14 mg, 0.1 mmol) was added thereto, and the mixture was stirred under ice-cooling for 30 min., and then at room temperature for 2 hrs. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried (over anhydrous Na2SO4), and the solvent was evaporated under reduced pressure. The residue was subjected to column chromatography using silica gel (10 g) and eluted with hexane-ethyl acetate (4:1, v/v) to give the title compound (30 mg, 84%) as an amorphous form.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred under ice-
  3. temperaturecooling for 30 min.
  4. waitat room temperature for 2 hrs
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe extract was dried (over anhydrous Na2SO4)
  7. customthe solvent was evaporated under reduced pressure
  8. washeluted with hexane-ethyl acetate (4:1

Sources & evidence

ORD record
ord-15254c6e64d542b2b8c71015b09d3313
Source dataset
uspto-grants-2011_05
Patent number
US07943770B2

Reaction notes

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