Process for preparing penicillin antibiotics

Details Process for preparing penicillin antibiotics Process for preparing penicillin antibiotics

1975-05-02

1976-07-27

Schwartz, Gerald A.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

C07D49968

Patent

active

039717755

ABSTRACT:
.alpha.-Aminoacylpenicillin antibiotics such as ampicillin and amoxycillin may be prepared in particularly simple manner by a process which comprises preparing a solution of 6-aminopenicillanic acid (6-APA) in a water-immiscible organic solvent by treating 6-APA with an excess of a strong tertiary amine base in the presence of said solvent; neutralising the residual strong tertiary amine base in said solution; reacting the neutralised solution with a solution in a water-immiscible organic solvent of an acylating agent which is a mixed anhydride of a lower alkoxyformic acid and an N-protected derivative of an .alpha.-aminoacid wherein the N-protecting group is acid-labile, to yield a solution of an N-protected .alpha.-aminoacylpenicillin derivative; contacting the resulting solution with water and a strong acid to cleave the acid-labile N-protecting group; and isolating the thus-obtained .alpha.-aminoacylpenicillin from the resulting water-containing system. The use of water-immiscible solvents in the process obviates the need for a solvent evaporation stage during isolation of the .alpha.-aminoacylpenicillin product and thus renders the process of particular advantage in plant-scale operations.

REFERENCES:
patent: 3846407 (1974-11-01), Huhn et al.

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