Methyl iodide → HCID 70112767, compound

HRID 324446Notes

Reaction equation

HRID 324446 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[NH:21][CH:22]=3)([OH:16])[C:10]3[N:11]=[C:12]([CH3:14])[O:13][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:25]=1.[H-].[Na+].[CH3:28]I>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15]([C:17]3[C:18](=[O:24])[NH:19][C:20](=[O:23])[N:21]([CH3:28])[CH:22]=3)([OH:16])[C:10]3[N:11]=[C:12]([CH3:14])[O:13][C:9]=3[CH2:8][CH2:7][C:6]=2[CH:25]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70113129HCID 70113129, compound

Product 1

HCID 70112767HCID 70112767, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the product from step (vii) (2.0 g) in tetrahydrofuran (20 ml) at 0° C. was added sodium hydride (60% dispersion by wt, 0.22 g). The mixture was stirred at 0° C. for 40 min and treated with methyl iodide (0.35 ml). The mixture was further stirred at 0° C. for 2 hours and room temperature for 24 hours then partitioned between ethyl acetate and water. The organic phase was washed with water and saturated brine, dried (MgSO4) and solvent evaporated. Purification was by chromatography eluting with 10% ethanol in dichloromethane to give the product as a pale yellow solid.

Workup

  1. stirringThe mixture was further stirred at 0° C. for 2 hours and room temperature for 24 hours
  2. customthen partitioned between ethyl acetate and water
  3. washThe organic phase was washed with water and saturated brine
  4. dry with materialdried (MgSO4) and solvent
  5. customevaporated
  6. customPurification
  7. washeluting with 10% ethanol in dichloromethane

Sources & evidence

ORD record
ord-61617e274e1141d9bc844b3972df0eb5
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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