Process for the production of p-(N-methyl)-aminobenzoyl-L-glutam

Details Process for the production of p-(N-methyl)-aminobenzoyl-L-glutam Process for the production of p-(N-methyl)-aminobenzoyl-L-glutam

1978-07-19

1980-07-08

Morgenstern, Norman

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

Organic compounds

Carboxylic acids and salts thereof

260544N, 562458, C07C10144

Patent

active

042118832

ABSTRACT:
Process for the production of p-(N-methyl)-amino-benzoyl-L-glutamic acid. The process includes introducing a formyl group into p-(N-methyl)-amino-benzoic acid, with p-(N-methyl-N-formyl)-aminobenzoic acid being formed. The p-(N-methyl-N-formyl)-aminobenzoic acid is chlorinated with a chloridizing agent, such as, sulfonyl chloride or thionyl chloride, with p-(N-methyl-N-formyl)-aminobenzoic acid chloride forming. The p-(N-methyl-N-formyl)-aminobenzoic acid chloride is reacted with L-glutamic acid in the presence of a base as an acid acceptor, with p-(N-methyl-N-formyl)-amino benzoyl-L-glutamic acid forming. The p-(N-methyl-N-formyl)-amino benzoyl-L-glutamic acid is converted into p-(N-methyl)-amino benzoyl-L-glutamic acid by alkaline hydrolysis in a 2.5 to 3.5 normal caustic soda solution at 30.degree. to 70.degree. C. Intermediates which are obtained include: p-(N-methyl-N-formyl)-aminobenzoic acid; p-(N-methyl-N-formyl)-aminobenzoic acid chloride; and p-(N-methyl-N-formyl)-amino benzoyl-L-glutamic acid.

REFERENCES:
patent: 3551419 (1970-12-01), Da Ra et al.
patent: 3892801 (1975-07-01), Kazan
Cosulich et al., J.A.C.S., vol. 70, pp. 1922-1926 (1948).
Fu et al., J. Org. Chem., vol. 30, pp. 1277-1278 (1965).
Santi, J. Heterocyc. Chem., vol. 4, pp. 475-481 (1967).
Seeger, J.A.C.S., vol. 71, pp. 1953-1958 (1949).
Fresin et al., Reagents for Organic Synthesis, p. 1158 (1965).
McOhme, Protective Groups in Organic Chemistry, pp. 46-53 (1974).
Abo-Sier et al., Chem. Abst., vol. 87, p. 432, #52897p (1977).

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