Sodium Hydroxide → (4S)-4-acetamido-5-fluoropentanoic acid

HRID 370621Notes

Reaction equation

HRID 370621 reaction equation
[OH-].[Na+].[C:3]([NH:6][C@H:7]([CH2:14][F:15])[CH2:8][CH2:9][C:10]([O:12]C)=[O:11])(=[O:5])[CH3:4]>CO>[C:3]([NH:6][C@H:7]([CH2:14][F:15])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])(=[O:5])[CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13477555(S)-4-(acetylamino)-5-fluoropentanoic acid, methyl ester

Product 1

HCID 13477559(4S)-4-acetamido-5-fluoropentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.2 ml of 1N aqueous sodium hydroxide solution was added drop-by-drop to 0.22 g of 6 in 2 ml of methanol and the resulting mixture was stirred for one hour at room temperature. The methanol was evaporated, water and ethyl acetate were added to the residue, and the resulting mixture was acidified with a few drops of 12N hydrochloric acid. The mixture was stirred at room temperature for 30 minutes, the organic layer was separated, dried (Na2SO4), and stripped of solvent under reduced pressure. The residue, an oil, was triturated with ether/pentane to give 7, as a light brown powder, m.p.: 80°-83° C.

Workup

  1. customThe methanol was evaporated
  2. additionwater and ethyl acetate were added to the residue
  3. stirringThe mixture was stirred at room temperature for 30 minutes
  4. customthe organic layer was separated
  5. dry with materialdried (Na2SO4)
  6. customThe residue, an oil, was triturated with ether/pentane
  7. customto give 7

Sources & evidence

ORD record
ord-48ebe825796b49278c2f47082cd92893
Source dataset
uspto-grants-1985_07
Patent number
US04528028

Reaction notes

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