Ethyl 4-[2-(diethylphosphonomethyl)phenyl]-2-acetamido-2-carboethoxybutanoate → 4-[2-Phosphonomethylphenyl]-2-aminobutanoic acid

HRID 542411Notes

Reaction equation

HRID 542411 reaction equation
C([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][C:18]([NH:29]C(=O)C)(C(OCC)=O)[C:19]([O:21]CC)=[O:20])([O:6]CC)=[O:5])C>Cl>[P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[CH2:16][CH2:17][CH:18]([NH2:29])[C:19]([OH:21])=[O:20])([OH:6])([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 13922737Ethyl 4-[2-(diethylphosphonomethyl)phenyl]-2-acetamido-2-carboethoxybutanoate

Product 1

HCID 139227384-[2-Phosphonomethylphenyl]-2-aminobutanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 2.5 g (5.3 mmol) of ethyl 4-[2-(diethylphosphonomethyl)-phenyl]-2-acetamido-2-carboethoxybutanoate in 50 mL of 6N HCl was stirred at vigorous reflux for 12 h. After cooling to room temperature the reaction mixture was concentrated at reduced pressure yielding an oil. This oil was washed with three 50 mL portions of water then dissolved in 95% ethanol and a slight excess of propylene oxide added. The precipitated acid was collected by filtration and recrystallized from dilute ethanol yielding 1.26 g (77%) of the product as a white solid: mp 247°-249° C. IR(KBr): 1725, 1620 cm-1 ; 1H NMR (D2O) δ 2.0-3.4 (6H unresolved), 3.9-4.3 (m, 1H), 7.4 (s, 4H); Anal. Calcd. for C11H16NO5P0.5H2O: Calcd: C, 46.62; H, 6.05; N, 4.94. Found: C, 46.73; H, 6.04; N, 4.79.

Workup

  1. temperatureat vigorous reflux for 12 h
  2. concentrationwas concentrated at reduced pressure
  3. customyielding an oil
  4. washThis oil was washed with three 50 mL portions of water
  5. dissolutionthen dissolved in 95% ethanol
  6. additiona slight excess of propylene oxide added
  7. filtrationThe precipitated acid was collected by filtration
  8. customrecrystallized from dilute ethanol yielding 1.26 g (77%) of the product as a white solid

Sources & evidence

ORD record
ord-eb9bfb6c6cc64a8597b554e74d46d9c0
Source dataset
uspto-grants-1987_04
Patent number
US04657899

Reaction notes

Loading…