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Preparation of N-(phosphonoacetyl)-L-aspartic acid

Assignee: Individual
•
Filing: 1978-08-10
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Granted: 1979-05-15
•
Expires: 1998-08-10
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Abstract

Abstract Improved methods for preparation of the tetrasodium and disodium salts of N-(phosphonoacetyl)-L-aspartic acid (PALA) are disclosed. The present methods are well suited for preparation of these products in large amounts. A particular aspect of these methods includes a water-ethanol washing procedure for reducing impurities, including acetic acid, sodium acetate and ethanol, to an acceptable level.

Inventors

  • 👤 Jack L. Parsons
  • 👤 Henryk Dubicki

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-05 17:07
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/28; C07F9/38; C07F9/3804; C07F9/3808

Claims Analysis

Total Claims: 2
Claim 1
Independent Claim 146 words
In a method for the preparation of a sodium salt of N-(phosphonoacetyl)-L-aspartic acid by reacting L-aspartic acid, dibenzyl ester p-toluenesulfonate with triethylamine, followed by the addition of phosphonoacetyl chloride to produce the N-(phosphonoacetyl)-L-aspartic acid moiety in the form of the dibenzyl ester, wherein the carboxyl groups of the N-(phosphonoacetyl)-L-aspartic acid are esterified, adding cyclohexylamine under anhydrous conditions to produce the cyclohexylamine salt of said dibenzyl ester, reacting said cyclohexylamine salt with sodium hydroxide to produce L-aspartic acid, N-(phosphonoacetyl)-, tetrasodium salt, and reacting said tetrasodium salt with acetic acid to produce L-aspartic acid, N-(phosphonoacetyl)-, disodium salt, the improvement which comprises subjecting the obtained disodium salt to a water-ethanol washing procedure, employing 92±1% by volume aqueous ethanol, said washing procedure being carried out at a temperature of from about 26° to about 28° C., thereby reducing impurities, including acetic acid, sodium acetate and ethanol, to an acceptable level.
Claim 2
Dependent Claim 146 words
In a method for the preparation of a sodium salt of N-(phosphonoacetyl)-L-aspartic acid by reacting L-aspartic acid, dibenzyl ester p-toluenesulfonate with triethylamine, followed by the addition of phosphonoacetyl chloride to produce the N-(phosphonoacetyl)-L-aspartic acid moiety in the form of the dibenzyl ester, wherein the carboxyl groups of the N-(phosphonoacetyl)-L-aspartic acid are esterified, adding cyclohexylamine under anhydrous conditions to produce the cyclohexylamine salt of said dibenzyl ester, reacting said cyclohexylamine salt with sodium hydroxide to produce L-aspartic acid, N-(phosphonoacetyl)-, tetrasodium salt, and reacting said tetrasodium salt with acetic acid to produce L-aspartic acid, N-(phosphonoacetyl)-, disodium salt, the improvement which comprises subjecting the obtained disodium salt to a water-ethanol washing procedure, employing 92±1% by volume aqueous ethanol, said washing procedure being carried out at a temperature of from about 26° to about 28° C., thereby reducing impurities, including acetic acid, sodium acetate and ethanol, to an acceptable level.

References Cited (Backward Citations)

US3417098A Cited
FR1488426A Cited
US4016148A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-05-14 1982-11-13 1983-05-15 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-05-14 1986-11-13 1987-05-15 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-05-14 1990-11-13 1991-05-15 $7700.00 Window Closed / Lapsed

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