HCID 14557564, compound → HCID 13922739, compound

HRID 542413Notes

Reaction equation

HRID 542413 reaction equation
C([O:3][P:4]([CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[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][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17][CH:18]([NH2:29])[C:19]([OH:21])=[O:20])([OH:6])([OH:5])=[O:3]

Participants

3

Reactant 1

HCID 14557564HCID 14557564, compound

Product 1

HCID 13922739HCID 13922739, compound

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of 7.9 g (16.8 mmol) of ethyl 3-[2-(2-diethylphosponoethyl)-phenyl]-2-acetamido-2-carboethoxypropanoate in 40 mL of 6N HCl was stirred at vigorous reflux for 14 h. After cooling to room temperature the reaction mixture was concentrated at reduced pressure yielding an oil. This oil was washed with four 25 mL portions of water then dissolved in 20 mL 95% ethanol and propylene oxide added dropwise. The precipitated crude acid was collected by filtration. Recrystallization from dilute ethanol yielded 4.1 g (90%) as a white solid, mp 241°-243° C. IR(Nujol): 1712.5 cm-1 (C=O). 1H NMR(D2O) δ 1.5-2.2 (m, 2H); 2.6-3.3 (m, 4H); 3.9-4.2 (t, 1H); 7.2 (m, 4H). Anal. Calcd. for C11H16NO5P: C, 48.35; H, 5.90; N, 5.13. Found: C, 48.69; H, 6.16; N, 4.95.

Workup

  1. temperatureat vigorous reflux for 14 h
  2. concentrationwas concentrated at reduced pressure
  3. customyielding an oil
  4. washThis oil was washed with four 25 mL portions of water
  5. dissolutionthen dissolved in 20 mL 95% ethanol
  6. additionpropylene oxide added dropwise
  7. customThe precipitated crude acid
  8. filtrationwas collected by filtration
  9. customRecrystallization from dilute ethanol
  10. customyielded 4.1 g (90%) as a white solid, mp 241°-243° C

Sources & evidence

ORD record
ord-b82ebb58b8c449ad87e9726c281ac0c0
Source dataset
uspto-grants-1987_04
Patent number
US04657899

Reaction notes

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