Amoxycillin synthesis

Piridicillin (27) is made by ]T-acylating amoxycillin with a rather complex acid. The synthesis begins by reacting j, ]i-diethanol amine with. c ty i zene-sul fonyl chloride to give 23. Conversion (to 24) with ethyl formate and sodium... 

The oral activity and clinical acceptance of cephalexin (14) has led to the appearance of a spate of similar molecules. Cefadroxyl (16) is an example. The design of this drug would seem to have derived from the success of amoxycillin. The synthesis of cefadroxyl was accomplished by N-acylation of 7-aminodesacetyl-cephalosporanic acid (7 ADCA) after blocking the carboxy group with (CH30)2CH3SiCl (to 15). The... 

Aminopyrine, 234 Aminotetradine, 265 2-Aminothiazole, 247 2-Aminothiazole synthesis, 126 Amisotetradine, 266 Amobarbital, 268 Amopyroquine, 342 Amoxycillin, 414 Amphetamine, 37, 70 Ampicillin, 413 Amprolium, 264 Amytriptylene, 141, 404 Anabolic effects, 169 Androgens, discovery, 155 Androstanolone, 173 Androstenedione, 158, 176 Anesthesia, parenteral, 56 Angst, 363 Anileridine, 300 Aniline, metabolism. 111 Anisindandione, 147 Anovlar , 186 Antagonists, 20, 65 Antazoline, 242 Antibodies, 41... 

Acylation of 6-APA with an amino acid leads to a compound that bears some resemblance to a dipeptide. The coupling product with D-phenylglycine shows an enhanced antibacterial spectmm, possibly as a result of a better fit to the cell wall cross-hnking enzyme. The compound also shows improved oral absorption. One synthesis starts with the acylation of 6-APA with the acid chloride (3-3) from D-2-azidophenylacetic acid. Catalytic reduction of the product (3-4) affords ampicillin (3-5) [4]. An analogous scheme leads to amoxycillin (3-6), a widely used dmg that is reasonably well absorbed on oral administration. 

Substituted hydantoin derivatives have been used as precursors for d- and L-amino acids in chemical synthesis. However, they are hydrolyzed enantioselectively by the enzymes named hydantoinases some act specifically on D-5-substituted hydantoins, and others on the L-isomers. N-Carbamoyl amino acids formed are also hydrolyzed enantiospecifically by N-carbamoyl amino acid amidohydrolases to produce d- or l-amino acids (Fig. 17-15). Since the Kanegafuchi Chemical Industry, Japan, commercialized an enzymatic procedure for the production of D-p-hydroxyphenylglycine, which is a building block for the semisynthetic P-lactam antibiotic amoxycillin, various processes for amino acid production by means of hydantoinases have been developed 131 133. ... 

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