HCID 23050913, compound → 4-Amino-5-fluoropentanoic acid

HRID 231335Notes

Reaction equation

HRID 231335 reaction equation
C(C[NH:5][CH:6]([CH2:12][F:13])[CH2:7][CH2:8][C:9]([OH:11])=[O:10])(O)=O>Cl>[NH2:5][CH:6]([CH2:12][F:13])[CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

3

Reactant 1

HCID 23050913HCID 23050913, compound

Product 1

HCID 1303634-Amino-5-fluoropentanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of 0.65 g (3.4 mmol) of 4-carboxymethylamino-5-fluoropentanoic acid and 10 ml of concentrated hydrochloric acid was prepared in a 50 ml flask and heated at reflux overnight. The volatiles were then removed by evaporation under reduced pressure and the gummy residue was dissolved in water and purified by ion exchange chromatography using DOWEX® 50 X-8 resin. The solution was loaded onto the rinsed column, washed with water, and eluted with 6 percent aqueous hydrochloric acid. Evaporation of the product-containing fractions gave 0.42 g (71 percent of theory) of the title compound as an oily crystalline material which tenaciously retained water. This was recrystallized from ethyl acetate/acetic acid to obtain the desired product as white crystals melting at 129°-134° C. and having the expected proton and carbon nmr spectra.

Workup

  1. customwas prepared in a 50 ml flask
  2. temperatureheated
  3. temperatureat reflux overnight
  4. customThe volatiles were then removed by evaporation under reduced pressure
  5. dissolutionthe gummy residue was dissolved in water
  6. custompurified by ion exchange chromatography
  7. washwashed with water
  8. washeluted with 6 percent aqueous hydrochloric acid
  9. customEvaporation of the product-containing fractions

Sources & evidence

ORD record
ord-13bcf58e0bc54dac97d1926c808c2dae
Source dataset
uspto-grants-1989_07
Patent number
US04845267

Reaction notes

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