The Nutrasweet Company

Nutrasweet Property Holdings, Inc.

Kenneth E Furlong

Indra Prakash

Handley E Jackson, Iii

Robert L Augustine

Setrak K Tanielyan

Robert C Scherm

Handley E Iii Jackson

N&#x2014;[N-(3,3-dimethylbutyl)-L-&#x3b1;-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-&#x3b1;-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N&#x2014;[N-(3,3-dimethylbutyl)-L-&#x3b1;-aspartyl]-L-phenylalanine 1-methyl ester synthesis.

Synthesis of N-[N-(3,3-dimethylbutyl)-L-&#x3b1;-aspartyl]-L-phenylalanine 1-methyl ester using 3,3-dimethylbutyraldehyde precursors

The present invention relates to a process of oxidation of alcohols selectively to aldehydes or ketones with molecular oxygen using a TEMPO based catalyst, Fe-bipyridyl or Fe-phenantroline co-catalyst and N-bromosuccinimide promoter in acetic acid solvent. The oxidation takes places at high rates and high aldehyde selectivity at temperatures in the range 45-50&#xb0; C. and oxygen or air pressures of 0-15 psi. The alcohol conversion of 95-100% and aldehyde selectivity higher than 95% are achieved over 3-4 hours reaction time. Aldehydes such as 3,3-dimethyl-1-butanal can be produced efficiently using the present invention.

Catalyst system for aerobic oxidation of primary and secondary alcohols

N-[N-(3,3-dimethylbutyl)-L-&#x3b1;-aspartyl]-L-phenylalanine 1-methyl ester is produced by hydrogenation of L-&#x3b1;-aspartyl-L-phenylalanine 1-methyl ester and 3,3-dimethylbutyraldehyde produced in situ by the hydrolysis or cleavage of a 3,3-dimethylbutyraldehyde precursor. The production method is efficient and low cost, as compared with conventional N-[N-(3,3-dimethylbutyl)-L-&#x3b1;-aspartyl]-L-phenylalanine 1-methyl ester synthesis.

The present invention relates to a process of oxidation of alcohols selectively to aldehydes or ketones with NaOCl using a TEMPO&mdash;borate catalyst system. It is shown that the oxidation can be efficiently carried out without KBr additives under solvent free conditions. Aldehydes such as 3,3-dimethylbutyraldehyde can be produced efficiently using the present invention.

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Evans, GA, United States of America

Kenneth E Furlong