تفاعل #739987

ord-1dfc1d035f4e483393eb913220bb37cd

معادلة التفاعل

O=C(Cl)COc1ccccc1
phenoxyacetyl chloride
CC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-ADCA
NC1C(=O)N2C(C(=O)OCc3ccccc3)=C(OS(=O)(=O)C(F)(F)F)CC[C@H]12
benzyl 7-amino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-ACA
→
O=C(COc1ccccc1)NC1C(=O)N2C(C(=O)OCc3ccccc3)=C(OS(=O)(=O)C(F)(F)F)CC[C@H]12
benzyl 7-phenoxyacetylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate

المتفاعلات

—
cephalosporin
O=C(Cl)COc1ccccc1
phenoxyacetyl chloride
CC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-ADCA
NC1C(=O)N2C(C(=O)OCc3ccccc3)=C(OS(=O)(=O)C(F)(F)F)CC[C@H]12
benzyl 7-amino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate
CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@@H](N)[C@H]2SC1
7-ACA

الكواشف

لا شيء

المذيبات

CC#N
acetonitrile
c1ccncc1
pyridine
CCN(CC)CC
triethylamine

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

الإجراء التجريبي

The N-acylations are carried out by using the methods employed for the acylation of the cephalosporin nuclei such as 7-ACA and 7-ADCA. In an example of the acylation benzyl 7-amino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate in acetonitrile is treated with phenoxyacetyl chloride in the presence of an acid-binding agent such as triethylamine or pyridine to provide benzyl 7-phenoxyacetylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylate.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04673737uspto-grants-1987_06