Methyl iodide → HCID 59773362, compound

HRID 2220753Notes

Reaction equation

HRID 2220753 reaction equation
[CH3:1][O:2][C:3](=[O:24])[C@H:4]([NH:16][C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:5][NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14].[H-].[Na+].[CH3:27]I.[NH4+].[Cl-]>CN(C=O)C>[CH3:1][O:2][C:3](=[O:24])[C@H:4]([NH:16][C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[CH2:5][N:6]([CH3:27])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59773356HCID 59773356, compound

Product 1

HCID 59773362HCID 59773362, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 eq of 177 in 20 mL of dry DMF was stirred at rt as 1.3 eq of NaH (60% in mineral oil) was added. After bubbling ceased (about 10 min), 1.1 eq of MeI was slowly added. After 18 h, 50 mL of sat. aq. NH4Cl was added to the reaction mixture. The mixture was extracted with EtOAc (3×50 mL). The combined organics were dried over MgSO4 and filtered. The filtrate was rotary evaporated. The crude material was flash chromatographed on silica using 20% EtOAc/hexanes as eluant. After concentration and drying under vacuum the fractions containing product afforded intermediate 178.

Workup

  1. additionwas added
  2. customAfter bubbling
  3. additionwas slowly added
  4. extractionThe mixture was extracted with EtOAc (3×50 mL)
  5. dry with materialThe combined organics were dried over MgSO4
  6. filtrationfiltered
  7. customchromatographed on silica using 20% EtOAc/hexanes as eluant
  8. concentrationAfter concentration
  9. customdrying under vacuum the fractions
  10. additioncontaining product

Sources & evidence

ORD record
ord-0ad94e4c3e68432bacf7c80b413b8457
Source dataset
uspto-grants-2008_08
Patent number
US07417152B2

Reaction notes

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