Réaction #1581872

ord-475a1fd31f0143658338a1c999fb1429

Équation de réaction

CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-amino-cephalosporanic acid
N[C@@H](C(=O)O)c1ccccc1
D-(-)-phenylglycine
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O
amoxycillin
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
ampicillin
→
CC1=C(C(=O)O)N2C(=O)[C@@H](NC(=O)[C@H](N)C3=CCC=CC3)[C@H]2SC1
cefradin

Réactifs

CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-amino-cephalosporanic acid
—
D-(-)-(4-hydroxyphenyl)-glycine
N[C@@H](C(=O)O)c1ccccc1
D-(-)-phenylglycine
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccc(O)cc3)C(=O)N2[C@H]1C(=O)O
amoxycillin
CC1(C)S[C@@H]2[C@H](NC(=O)[C@H](N)c3ccccc3)C(=O)N2[C@H]1C(=O)O
ampicillin
—
D-(-)-2-amino-2-(1,4-cylcohexadien-1-yl)acetic acid

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

As an example, D-(-)-(4-hydroxyphenyl)-glycine and D-(-)-phenylglycine are key intermediates in the industrial synthesis of amoxycillin and ampicillin respectively; while D-(-)-2-amino-2-(1,4-cylcohexadien-1-yl)acetic acid may conveniently be employed in the acylation of 7-amino-cephalosporanic acid to give cefradin.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05026906uspto-grants-1991_06