Hydrochloric Acid → 3-(Phosphonoacetyl)piperidine-2-carboxylic acid

HRID 1614047Notes

Reaction equation

HRID 1614047 reaction equation
C([O:8][C:9]([CH:11]1[CH:16]([C:17](=[O:27])[CH2:18][P:19]([O:24]CC)([O:21]CC)=[O:20])[CH2:15][CH2:14][CH2:13][N:12]1C(OCC1C=CC=CC=1)=O)=[O:10])C1C=CC=CC=1.Cl.C(O)C>C(O)(C)C>[P:19]([CH2:18][C:17]([CH:16]1[CH2:15][CH2:14][CH2:13][NH:12][CH:11]1[C:9]([OH:10])=[O:8])=[O:27])([OH:21])([OH:24])=[O:20]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 15030796HCID 15030796, compound

Product 1

HCID 1321723-(Phosphonoacetyl)piperidine-2-carboxylic acidYield 91.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Mix N-carbobenzoxy-3[(diethoxyphosphinyl)acetyl]piperidine-2-carboxylic acid benzyl ester (3.6 g) and 6N hydrochloric acid (400 mL) and reflux for 24 hours. Condense with a stream of nitrogen and dissolve the residue in a mixture of absolute ethanol (75 mL) and isopropanol (75 mL). Filter and add propylene oxide until a white precipitate develops. Filter the precipitate, wash with isopropanol and dry to give the title compound as a white powder (1.55 g, 91%).

Workup

  1. temperaturereflux for 24 hours
  2. customCondense with a stream of nitrogen
  3. dissolutiondissolve the residue
  4. filtrationFilter
  5. additionadd propylene oxide until a white precipitate
  6. filtrationFilter the precipitate
  7. washwash with isopropanol
  8. customdry

Sources & evidence

ORD record
ord-f6e33093e6f44441b2a64127dac55a2e
Source dataset
uspto-grants-1993_03
Patent number
US05194430

Reaction notes

Loading…