Synthesis of N-benzyloxycarbonyl-L-aspartic acid

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United States of America Patent

PATENT NO 4523026
SERIAL NO

06526581

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N-Benzyloxycarbonyl-L-aspartic acid (Z-Asp) is synthesized by adding benzyl chloroformate to a solution of L-aspartic acid and sodium hydroxide at relatively high temperatures of 35.degree.-55.degree. C. and over a wide pH range of 9.2-12.0 and acidifying the sodium salt product. The Z-Asp is prepared in high yields exceeding 90% and purity of better than 99% with only a minor amount of the by-product N-benzyloxycarbonyl aspartyl aspartic acid. The Z-Asp is suitable for conversion to aspartame. Carrying out the reaction at high temperatures significantly reduces cycle time while maintaining a high yield with a low dipeptide and unreacted L-aspartic acid content.

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MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY1295 STATE STREET SPRINGFIELD MA 01111-0001
MASSMUTUAL PARTICIPATION INVESTORS1295 STATE ST C/O MASSACHUSETTS MUTAL LIFE INSURANCE COMPANY SPRINGFIELD MA 01111
PNC BANK N A AS PER AGENT FOR OTHER SECURED PARTIES ON ATTACHED SHEET2 TOWER CENTER EAST BRUNSWICK NJ 08816
CM LIFE INSURANCE COMPANY C/O MASSACHUSETTS MUTUAL LIFE INSURANCE COMPANY1295 STATE STREET SPRINGFIELD MA 01111
MASSMUTUAL CORPORATE VALUE PARTNERS LIMITEDP O BOX 1092 GEORGE TOWN C/O BANK OF AMERICA TRUST AND BANKING CORPORATION GRAND CAYMAN B W I

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Inventor(s)

Inventor Name Address # of filed Patents Total Citations
Chen, Mary S Edison, NJ 4 8
Pendse, Anil D Highland Park, NJ 1 0
Wan, K Ming East Brunswick, NJ 3 0

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