Methyl iodide → HCID 18791534, compound

HRID 1005584Notes

Reaction equation

HRID 1005584 reaction equation
[H-].[Na+].[CH2:3]([O:10][C:11]1[CH:31]=[CH:30][CH:29]=[CH:28][C:12]=1[C:13]([NH:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27])=[O:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:32]I>CN(C)C=O>[CH3:32][N:15]([C:13](=[O:14])[C:12]1[CH:28]=[CH:29][CH:30]=[CH:31][C:11]=1[O:10][CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1)[C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 18791398HCID 18791398, compound

Product 1

HCID 18791534HCID 18791534, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride (60% oil suspension, 88.3 mg) in N,N-dimethylformamide (6 ml) was added a solution of methyl 4-(2-benzyloxybenzoyl)amino-3-methoxybenzoate (600 mg) in N,N-dimethylformamide (4 ml) and the mixture was stirred at 0° C. for 1 hour. Methyl iodide (0.14 ml) was added dropwise to the above solution and the mixture was stirred at 0° C. for 30 minutes. The reaction temperature was raised to ambient temperature over 30 minutes and the reaction was quenched with 1 N hydrochloric acid, and then the resulting solution was extracted with ethyl acetate. Drying, filtering and removal of solvents afforded a crude product. The crude product was purified by column chromatography (eluent; hexane:ethyl acetate=3:1) to give methyl 4-(N-methyl-2-benzyloxybenzoylamino)-3-methoxybenzoate (650 mg).

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. temperatureThe reaction temperature was raised to ambient temperature over 30 minutes
  3. customthe reaction was quenched with 1 N hydrochloric acid
  4. extractionthe resulting solution was extracted with ethyl acetate
  5. customDrying
  6. filtrationfiltering
  7. customremoval of solvents
  8. customafforded a crude product
  9. customThe crude product was purified by column chromatography (eluent; hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-0ab2d6641b0d45a399a7703dc924a64d
Source dataset
uspto-grants-2000_04
Patent number
US06054457

Reaction notes

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