Ethyl Acetate → HCID 22032893, compound

HRID 1791403Notes

Reaction equation

HRID 1791403 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=3)[NH:14][N:13]=2)=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])[CH:2]([CH3:4])[CH3:3].[C:27]([O:33][CH2:34]Cl)(=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C=O)C>[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[N:16]=[C:15]([C:17]3[CH:22]=[CH:21][N:20]=[C:19]([CH3:23])[CH:18]=3)[N:14]([CH2:34][O:33][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[N:13]=2)=[CH:8][C:7]=1[N+:24]([O-:26])=[O:25])[CH:2]([CH3:4])[CH3:3]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 87885Chloromethyl pivalateHCID 10286846HCID 10286846, compound

Product 1

HCID 22032893HCID 22032893, compoundYield 76.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

354 mg of the powder obtained in Example 1 was dissolved in 3 ml of DMF, 181 mg of pivaloyloxymethyl chloride and 276 mg of potassium carbonate were added thereto, and the mixture was stirred at room temperature for 18 hours. Ethyl acetate was added to the reaction mixture, which was then washed with water and dried over magnesium sulfate. After the magnesium sulfate was filtered off, the solvent was evaporated under reduced pressure and the residue was subjected to silica gel column chromatography. Chloroform-acetone (95:5) was used as an eluent and 358 mg of the object compound was obtained as a white powder.

Workup

  1. washwas then washed with water
  2. dry with materialdried over magnesium sulfate
  3. filtrationAfter the magnesium sulfate was filtered off
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-b0c8094aa6dc4e63a19a2e4759db5c4b
Source dataset
uspto-grants-2006_07
Patent number
US07074816B2

Reaction notes

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