Potassium Iodide → HCID 15670373, compound

HRID 248699Notes

Reaction equation

HRID 248699 reaction equation
[Na+].[C:2]([O:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([O-:15])=[O:14])=[O:8])([CH3:5])([CH3:4])[CH3:3].CN(C=O)C.[I-].[K+].[C:26]([O:32][CH2:33]Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28]>C(OCC)(=O)C>[C:2]([O:6][C:7]([NH:9][C:10]1[CH:11]=[C:12]([CH:16]=[CH:17][CH:18]=1)[C:13]([O:15][CH2:33][O:32][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[O:14])=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6228DimethylformamideHCID 87885Chloromethyl pivalateHCID 70092594HCID 70092594, compound

Product 1

HCID 15670373HCID 15670373, compoundYield 87.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

3-(t-Butyloxycarbonylamino)benzoic acid sodium salt (10 g), DMF (60 ml) and potassium iodide (6.3 g) are mixed, and thereto is added dropwise pivaloyloxymethyl chloride (6 g) under ice cooling. The mixture is stirred at room temperature for 15 hours, and thereto is added ethyl acetate (200 ml). The mixture is washed with water, and ethyl acetate is distilled off under reduced pressure. The residue is recrystallized from 70% aqueous acetonitrile to give pivaloyloxymethyl 3-(t-butyloxycarbonylamino)benzoate (11.9 g).

Workup

  1. washThe mixture is washed with water, and ethyl acetate
  2. distillationis distilled off under reduced pressure
  3. customThe residue is recrystallized from 70% aqueous acetonitrile

Sources & evidence

ORD record
ord-7fbd2cb721464e40bcaec4f3154bb62f
Source dataset
uspto-grants-1993_05
Patent number
US05210266

Reaction notes

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