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filingDate 1975-05-02-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1976-07-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0dddf35ab80516a350c60024e6a83c4f
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_7fabaac532d494f9ca9081b19adc3c30
publicationDate 1976-07-27-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber US-3971775-A
titleOfInvention Process for preparing penicillin antibiotics
abstract α-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 α-aminoacid wherein the N-protecting group is acid-labile, to yield a solution of an N-protected α-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 α-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 α-aminoacylpenicillin product and thus renders the process of particular advantage in plant-scale operations.
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