Method of preparation of 2-phosphate esters of ascorbic acid

Details Method of preparation of 2-phosphate esters of ascorbic acid Method of preparation of 2-phosphate esters of ascorbic acid

1978-06-01

1979-12-18

Milestone, Norma S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

2603437, C07F 909

Patent

active

041794451

ABSTRACT:
A method of preparing nutritionally useful 2-phosphated ester derivatives of ascorbic acid in extremely high yields is disclosed which includes steps of reacting an ascorbic acid such as L-ascorbic acid or a derivative such as 5,6-O-isopropylidene-L-ascorbic acid with a phosphorylating agent in the presence of a tertiary amine while maintaining the pH of the reaction mixture at a level of at least about 8 for achieving almost quantitative 2-phosphorylation of the ascorbic acid derivative. In preferred forms 5,6-O-isopropylidene-L-ascorbic acid is reacted in water with phosphorous oxychloride in the presence of about a fivefold excess of pyridine relative to the acid and at low temperatures (-5 to +5.degree. C.); an alkali metal hydroxide such as potassium hydroxide is added to the reaction mixture as needed for maintaining the pH thereof at a level of about 12-13 during the entire phosphorylation reaction. Production of the diester of the ascorbic acid derivative can be selectively increased by omitting the tertiary amine from the reaction mixture and conducting the reactant at an elevated temperature of from about 30.degree.-60.degree. C.

REFERENCES:
patent: 3658848 (1972-04-01), Nomura et al.
patent: 3671549 (1972-06-01), Hinkley
patent: 3718482 (1973-02-01), Hinkley
Cutolo et al., Gazz. Chim. Ital., vol. 91 (1961) pp. 964-972.
Chemical Abstracts, vol. 79, 66743 g, abstracting Jap. Pat. 73-15605, May 16, 1973.

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