Ethyl 3-[2-(diethylphosphonopropyl)phenyl]-2-acetamido-2-carboethoxypropanoate → 3-[2-(3-Phosphonopropyl)phenyl]-2-aminopropanoic acid

HRID 542417Notes

Reaction equation

HRID 542417 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][C:19]([NH:30]C(=O)C)(C(OCC)=O)[C:20]([O:22]CC)=[O:21])([O:6]CC)=[O:5])C>Cl>[P:4]([CH2:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[CH2:18][CH:19]([NH2:30])[C:20]([OH:22])=[O:21])([OH:6])([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 20208634Ethyl 3-[2-(diethylphosphonopropyl)phenyl]-2-acetamido-2-carboethoxypropanoate

Product 1

HCID 139227413-[2-(3-Phosphonopropyl)phenyl]-2-aminopropanoic acid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 3.0 g (6.9 mmol) of ethyl 3-[2-(diethylphosphonopropyl)phenyl]-2-acetamido-2-carboethoxypropanoate in 25 mL of 6N HCl was stirred at vigorous reflux 12 h. After cooling to room temperature the reaction mixture was concentrated at reduced pressure yielding an oil. The oil was washed with three 25 mL portions of water then dissolved in 25 mL 95% ethanol and propylene oxide added dropwise. The precipitated acid was collected by filtration. Recrystallization from dilute ethanol yield 0.76 g (38%) as a white solid mp>95° C. (dec.). IR(nujol): 1717.6 cm-1 (C=O). 1H NMR(D2O) δ 1.1-2.0 (complex m, 4H); 2.6-3.1 (m, 4H); 3.35-3.65 (m, 1H); 7.3 (m, 4H). Anal. Calcd. for: C12H18NO5P.H2O: C, 47.21; H, 6.60; N, 4.58. Found: C, 47.47; H, 6.72; N, 4.53.

Workup

  1. temperatureat vigorous reflux 12 h
  2. concentrationwas concentrated at reduced pressure
  3. customyielding an oil
  4. washThe oil was washed with three 25 mL portions of water
  5. dissolutionthen dissolved in 25 mL 95% ethanol
  6. additionpropylene oxide added dropwise
  7. filtrationThe precipitated acid was collected by filtration
  8. customRecrystallization from dilute ethanol yield 0.76 g (38%) as a white solid mp>95° C. (dec.)

Sources & evidence

ORD record
ord-99b10018677e47039d253d051692a769
Source dataset
uspto-grants-1987_04
Patent number
US04657899

Reaction notes

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