Acetic Acid → 5,5-Difluoro-4-[(methoxycarbonyl)amino]pentanoic acid

HRID 1903244Notes

Reaction equation

HRID 1903244 reaction equation
[F:1][CH:2]([F:12])[CH:3]([NH:7][C:8]([O:10][CH3:11])=[O:9])[CH2:4]C=C.[Mn]([O-])(=O)(=O)=O.[K+].[C:19]([OH:22])(=[O:21])[CH3:20]>O>[F:1][CH:2]([F:12])[CH:3]([NH:7][C:8]([O:10][CH3:11])=[O:9])[CH2:4][CH2:20][C:19]([OH:22])=[O:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 20468434HCID 20468434, compound

Product 1

HCID 132733245,5-Difluoro-4-[(methoxycarbonyl)amino]pentanoic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

1,1-Difluoro-2-methoxycarbonylamino-4-pentene prepared as in Step F (4.00 g, 20.7 mM), dissolved in glacial acetic acid (60 ml), is added to potassium permanganate (9.80 g, 62 mM) in water (300 ml) at 0° C. After stirring for 15 hours at room temperature, the excess of potassium permanganate is destroyed with a 10% sodium bisulfite solution and the mixture saturated with sodium chloride. Extraction with diethyl ether and evaporation of the solvent in vacuo affords 1,1-difluoro-2-methoxycarbonylamino-5-pentanoic acid as a colorless oil. Crystallization from ether/petroleum ether gives 3.200 g of pure acid.

Workup

  1. customthe excess of potassium permanganate is destroyed with a 10% sodium bisulfite solution
  2. extractionExtraction
  3. customwith diethyl ether and evaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-6cdc7120d04148f8a0e3cf04b9ce7dff
Source dataset
uspto-grants-1984_03
Patent number
US04435425

Reaction notes

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