Organic compounds -- part of the class 532-570 series – Organic compounds – Carboxylic acid esters
Reexamination Certificate
2000-04-14
2004-08-31
Gitomer, Ralph (Department: 1627)
Organic compounds -- part of the class 532-570 series
Organic compounds
Carboxylic acid esters
C560S041000
Reexamination Certificate
active
06784309
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
This invention relates to an improved method for the purification of an N-alkylated aspartame derivative, which is a particularly useful sweetening agent.
2. Related Background Art
N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (neotame) is a high potency dipeptide sweetener (about 8000X sweeter than sucrose) that has the formula
The synthesis of neotame is disclosed in U.S. Pat. No. 5,480,668, U.S. Pat. No. 5,510,508 and U.S. Pat. No. 5,728,862, the disclosure of each of which is incorporated by reference herein. These processes, however, may produce several impurities, including N,N-di(3,3-dimethylbutyl)-L-aspartyl-L-phenylalanine methyl ester (dialkylated aspartame), &agr;-methyl hydrogen-3-(3,3-dimethylbutyl)-2-L-(2,2-dimethylpropyl)-5-oxo-&agr;-L-(phenylmethyl)-1,4(L)-imidazolidine diacetate (dialkylated imidazolidinone), N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine (demethylated &agr;- or &bgr;-neotame) and methyl ester of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester (methylated &agr;- or &bgr;-neotame). These impurities are represented respectively by the structural formulae:
The primary impurities generated in the synthesis of N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester, i.e., dialkylated aspartame, methyl ester of &agr;-neotame and dialkylated imidazolidinone, have very similar solubilities compared to N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester and thus are difficult to remove by crystallization, thereby making it difficult to obtain pure product in high yield.
Since neotame is mainly employed in foods for human consumption, it is extremely important that neotame exist in a highly purified state. Thus, it is clear that there is a need to economically produce pure N-[N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester.
SUMMARY OF THE INVENTION
This invention is directed to a process of purifying [N-(3,3-dimethylbutyl)-L-&agr;-aspartyl]-L-phenylalanine 1-methyl ester. The process comprises the steps of: (a) washing neotame with water; (b) combining the water washed neotame with an organic solvent to form a slurry; and (c) filtering the slurry to recover purified neotame. The organic solvent of step (b) may be an aqueous organic solvent.
Preferably, the process includes the steps of washing the neotame recovered in step (c) with an organic solvent, which may be the same or different than the organic solvent of step (b) and drying the washed filtered slurry to recover further purified neotame.
REFERENCES:
patent: 5480668 (1996-01-01), Nofre et al.
patent: 5510508 (1996-04-01), Claude et al.
patent: 5728862 (1998-03-01), Prakash
patent: 99/58554 (1999-11-01), None
Derwent abstract (Acc No. 1999-244007) of JP 11080108. Takemoto (1999). Purifying N-[N-(3,3-dimethylbutyl)-L-a-aspartyl]-L-phenylalanine 1-methyl ester, by two phase solvent extraction.*
Caplus abstract (1999:206867) of JP 1180108. Takemoto (1999). Purification and recovery of N-[N-(3,3-dimethylbutyl)-L-a-aspartyl]-L-phenylalanine 1-methyl ester as sweetener.
Prakash Indra
Wachholder Kurt
Gitomer Ralph
Hoster Jeffrey M
The Nutrasweet Company
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