Reacción #55517

ord-6f723c98875445248f0a9e19d810883a

Ecuación de reacción

C=C(C)[C@H](C(=O)OC(c1ccccc1)c1ccccc1)N1C(=O)[C@@H]2N=C(c3ccccc3)O[C@@H]21
Compound ( 1a )
C=C(C)[C@H](C(=O)OC(c1ccccc1)c1ccccc1)N1C(=O)[C@@H]2N=C(c3ccccc3)O[C@@H]21
diphenylmethyl (2R)-3-methyl-2-((1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-3-butenoate
ClCl
chlorine
c1ccncc1
pyridine
→
C=C(CCl)[C@H](C(=O)OC(c1ccccc1)c1ccccc1)N1C(=O)[C@@H]2N=C(c3ccccc3)O[C@@H]21
Compound ( 7 )
C=C(CCl)[C@H](C(=O)OC(c1ccccc1)c1ccccc1)N1C(=O)[C@@H]2N=C(c3ccccc3)O[C@@H]21
diphenylmethyl (2R)-2-[(1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicylo[3,2,0]hept-2-en-6-yl]-3-chloromethyl-3-butenoate

Reactantes

C=C(C)[C@H](C(=O)OC(c1ccccc1)c1ccccc1)N1C(=O)[C@@H]2N=C(c3ccccc3)O[C@@H]21
Compound ( 1a )
C=C(C)[C@H](C(=O)OC(c1ccccc1)c1ccccc1)N1C(=O)[C@@H]2N=C(c3ccccc3)O[C@@H]21
diphenylmethyl (2R)-3-methyl-2-((1R,5S)-3-phenyl-7-oxo-4-oxa-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl)-3-butenoate
ClCl
chlorine
c1ccncc1
pyridine

Reactivos

Ninguno

Disolventes

CCOC(C)=O
ethyl acetate
ClC(Cl)(Cl)Cl
carbon tetrachloride

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Procedimiento

A solution of 100 mg of Compound (1a) in ethyl acetate is reacted with a solution (2.0 molar equivalents) of chlorine in carbon tetrachloride at room temperature. The obtained product is treated with 1.2 equivalents of pyridine for 45 minutes under ice cooling, instead of chromatography of silica gel, to yield 110 mg of Compound (7).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04220766uspto-grants-1980_09