Synthesis of N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester using L-α-aspartyl-L-phenylalanine 1-methyl ester precursors
AssigneeThe NutraSweet Company
InventorsIndra Prakash, Zhi Guo, Steve Schroeder, Kurt L. Wachholder
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Abstract
N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of a mixture of 3,3-dimethylbutyraldehyde and a precursor of L-α-aspartyl-L-phenylalanine 1-methyl ester. In particular, N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester is produced using an acid salt of L-α-aspartyl-L-phenylalanine 1-methyl ester or N-protected L-α-aspartyl-L-phenylalanine 1-methyl ester. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester synthesis.
Claims35
A process of synthesizing N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester comprising reacting an isolated acid salt of L-α-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde in a solvent in the presence of a catalyst and hydrogen and in the absence of an acid for a time and at a temperature sufficient to produce N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester.
A process of synthesizing N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester comprising reacting an admixture of N-protected L-α-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde in a solvent in the presence of a catalyst and in the presence of hydrogen for a time and at a temperature sufficient to produce N-[N-(3,3-dimethylbutyl)-L-α-aspartyl]-L-phenylalanine 1-methyl ester that is greater than 98% pure, wherein the 3,3-dimethylbutyraldehyde is added gradually.
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