Methyl iodide → HCID 54476463, compound

HRID 1377711Notes

Reaction equation

HRID 1377711 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[H-].[Na+].[CH3:26]I>CN(C=O)C>[CH3:26][O:1][C:2]1[CH:11]=[C:10]([O:12][CH:13]2[CH2:16][N:15]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[CH2:14]2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 54498210HCID 54498210, compound

Product 1

HCID 54476463HCID 54476463, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of methyl 2-hydroxy-4-(1-tert-butyloxycarbonyl-3-azetidinyloxy)benzoate from Step 3 above (1.30 g, 4.02 mmol) in DMF (40 mL) under N2 was added NaH (241 mg, 6.03 mmol). The reaction mixture was cooled, and CH3I (0.50 mL, 8.04 mmol) was added via syringe. The reaction mixture was allowed to warm to ambient temperature, then stirred for an additional 2 hours. The solvent was removed under reduced pressure and the residue was partitioned between ethyl acetate and aqueous NaHCO3. The ethyl acetate layer was dried (MgSO4), filtered, and evaporated under reduced pressure. The residue was purified using pressurized silica gel column chromatography, eluting with 20% ethyl acetate in hexanes. Methyl 2-methoxy-4-(1-tert-butyloxycarbonyl-3-azetidinyloxy)benzoate was obtained as a colorless oil which crystallized on standing overnight.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customThe solvent was removed under reduced pressure
  3. customthe residue was partitioned between ethyl acetate and aqueous NaHCO3
  4. dry with materialThe ethyl acetate layer was dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified
  8. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-b6369dec96854a55b70a02ca49853bf2
Source dataset
uspto-grants-1997_09
Patent number
US05665719

Reaction notes

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