Methyl iodide → HCID 69818100, compound

HRID 2417427Notes

Reaction equation

HRID 2417427 reaction equation
C([O:4][CH2:5][C@@H:6]([N:23]([CH2:31][C@H:32]([O:41]C(=O)C)[CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([NH:14][C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:10][CH:9]=1)(=O)C.[H-].[Na+].I[CH3:48]>O1CCCC1>[CH2:24]([N:23]([C@H:6]([CH2:5][OH:4])[CH2:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]([CH3:48])[C:15](=[O:22])[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:12][CH:13]=1)[CH2:31][C@H:32]([OH:41])[CH2:33][O:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 69817644HCID 69817644, compound

Product 1

HCID 69818100HCID 69818100, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To an ice-cooled solution of N-[4-[(2S)-3-acetoxy-2-[N-[(2S)-2-acetoxy-3-phenoxypropyl]-N-benzylamino]propyl]-phenyl]benzamide (107 mg) in tetrahydrofuran (1.1 ml) was added sodium hydride (60% in oil, 17 mg), and the mixture was stirred at the same temperature for 30 minutes. To the mixture was added iodomethane (25 μl), and the mixture was stirred at room temperature for 1.5 hours before being partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was dissolved in methanol (1.1 ml)-1,4-dioxane (1.1 ml), then treated with 1N sodium hydroxide (0.5 ml) at room temperature for 1.5 hours. The mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate, and filtered. The filtrate was concentrated and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate) to give N-[4-[(2S)-2-[N-benzyl-N-[(2S)-2-hydroxy-3-phenoxypropyl]-amino]-3-hydroxypropyl]phenyl]-N-methylbenzamide (55 mg) as a white amorphous powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. custombefore being partitioned between ethyl acetate and water
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated
  8. dissolutionthe residue was dissolved in methanol (1.1 ml)-1,4-dioxane (1.1 ml)
  9. additiontreated with 1N sodium hydroxide (0.5 ml) at room temperature for 1.5 hours
  10. concentrationThe mixture was concentrated
  11. custompartitioned between ethyl acetate and water
  12. customThe organic layer was separated
  13. washwashed with brine
  14. dry with materialdried over magnesium sulfate
  15. filtrationfiltered
  16. concentrationThe filtrate was concentrated
  17. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate)

Sources & evidence

ORD record
ord-f2aa0d2882544fefb761f55fa19dd340
Source dataset
uspto-grants-2004_11
Patent number
US06826033B2

Reaction notes

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