Process for racemizing an optically active N-benzylidene amino-a

Details Process for racemizing an optically active N-benzylidene amino-a Process for racemizing an optically active N-benzylidene amino-a

1986-04-10

1989-07-11

Raymond, Richard L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Amino nitrogen containing

564160, 564165, 564198, 548344, 548491, C07C10328

Patent

active

048474126

ABSTRACT:
The invention relates to a process for racemizing an optically active N-benzylidene amino-acid amide, characterized in that a solution of the N-benzylidene amino-acid amide is mixed in a water-miscible organic solvent with at least 0.05 mole strong base per liter solution.
The invention further relates to a process for preparing an L-amino acid by enzymatic separation of the corresponding DL-amino-acid amide with an enzyme preparation from Pseudomonas putida, in which process also unconverted D-amino-acid amide is left behind in solution, characterized in that benzaldehyde is added to the solution, during which addition a precipitate of D-N-benzylidene amino-acid amide is being formed, this precipitate is subsequently, after being separated off, dissolved in an acetone-water mixture, 0.08-0.15 mole KOH/liter solution is subsequently added, the resulting solution is stirred for 1-20 hours at 20.degree.-60.degree. C., sulphuric acid is then added until the pH of the solution is 5 and the resulting sulphuric acid salt of the DL-amino-acid amide is finally, after isolation at pH 8-10, converted into the DL-amino-acid amide and this DL-amino-acid amide is used again.

REFERENCES:
patent: 440792 (1985-10-01), Commeyras et al.
patent: 4172846 (1979-10-01), Boesten
patent: 4275217 (1981-06-01), Duhamel et al.
patent: 4401820 (1983-08-01), Chibata et al.
patent: 4713470 (1987-12-01), Mirviss

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