Reacción #55519

ord-5171c4ce16e741f8a4f5e089cf8bb0d1

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
→
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

—
solution
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

Reactivos

Ninguno

Disolventes

ClCCl
methylene chloride
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 3 ml of methylene chloride is mixed with 0.2 ml of a 1.66 N solution of chlorine in carbon tetrachloride at 38° C. with stirring under nitrogen atmosphere to yield Compound (7) after silica gel chromatography.

Fuente

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