Process for the preparation of (6S)- and (6R)-tetrahydrofolic ac

Details Process for the preparation of (6S)- and (6R)-tetrahydrofolic ac Process for the preparation of (6S)- and (6R)-tetrahydrofolic ac

1993-04-08

1994-06-28

Daus, Donald G.

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

Organic compounds

Four or more ring nitrogens in the bicyclo ring system

C07D47504

Patent

active

053248368

ABSTRACT:
For the preparation of (6S)- and (6R)-tetrahydrofolic acid and their addition salts with a sulfonic acid or with sulfuric acid, (6R,S)-tetrahydrofolic acid is reacted with a sulfonic acid or with sulfuric acid, the resulting acid addition salt is fractionally crystallized and, if desired, the (6S)- or (6R)-tetrahydrofolic acid is liberated from the resulting diastereomeric acid addition salts by treatment with a base and isolated.

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Abstract of JP 73-0312120 (Eisai) 1973.
Temple, Jr. et al., "Preparation and Purification of L-(+)-5-Formyl-5, 6,7,8-tetrahydrofolic Acid," Journal of Medicinal Chemistry, vol. 22, No. 6, Jun. 1979, pp. 731-734.
Rees et al., "Asymmetric Reduction of Dihydrofolate Using Dihydrofolate Reductase and Chiral Boron-Containing Compounds," Tetrahedron, vol. 41, No. 1, 1986, pp. 117-136.
Feeney et al., "Hydrogen-1 Nuclear Magnetic Resonance Study of the Complexes of Two Diastereoisomers of Folinic Acid with Dihydrofolate Reductase," Biochemistry, vol. 20, No. 7, 1981, pp. 1837-1842.
Kwee et al., "Asymmetric Reduction of L-Folic Acid at Chiral Electrodes," Bioelectrochemistry and Bioenergetics, vol. 7, 1980, pp. 693-698, J. Electroanal. Chem., vol. 116, 1980, pp. 693-698.
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