Sodium Hydroxide → (S)-4-((2,4-dichlorophenoxyacetyl)amino)-5-fluoropentanoic acid

HRID 370625Notes

Reaction equation

HRID 370625 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][C:8]([NH:10][C@H:11]([CH2:18][F:19])[CH2:12][CH2:13][C:14]([O:16]C)=[O:15])=[O:9]>CO>[Cl:3][C:4]1[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:5]=1[O:6][CH2:7][C:8]([NH:10][C@H:11]([CH2:18][F:19])[CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[O:9]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13477575(S)-4-((2,4-dichlorophenoxyacetyl)amino)-5-fluoropentanoic acid, methyl ester

Product 1

HCID 13477577(S)-4-((2,4-dichlorophenoxyacetyl)amino)-5-fluoropentanoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

0.77 ml of 1N aqueous sodium hydroxide solution was added to a stirred mixture of 0.27 g of 16 in 20 ml of methanol, the resulting mixture was stirred at reflux for one hour and then at room temperature over a week-end. The mixture then was filtered and the solvent evaporated from the filtrate. The residue was placed in water, ethyl acetate was added, then the mixture was acidified with 12N hydrochloric acid. The mixture was stirred for 30 minutes, then the organic phase was separated, dried (Na2SO4) and filtered. The solvent was evaporated from the filtrate to give a pale yellow oil. The oil was filtered through a florosil pad, eluted with ethyl acetate to give an oily solid, which was treated with methanol to give 17, as a white solid.

Workup

  1. temperatureat reflux for one hour
  2. waitat room temperature over a week-end
  3. filtrationThe mixture then was filtered
  4. customthe solvent evaporated from the filtrate
  5. additionethyl acetate was added
  6. stirringThe mixture was stirred for 30 minutes
  7. customthe organic phase was separated
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. customThe solvent was evaporated from the filtrate
  11. customto give a pale yellow oil
  12. filtrationThe oil was filtered through a florosil pad
  13. washeluted with ethyl acetate
  14. customto give an oily solid, which

Sources & evidence

ORD record
ord-392582d4f4fe4bc08e7abe139b014960
Source dataset
uspto-grants-1985_07
Patent number
US04528028

Reaction notes

Loading…