Reacción #413369

ord-215fdbdafc56419f928c688910451e4b

Ecuación de reacción

$CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1$

(5Z,13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid methylsulfonylamide

→

$CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1O$

desired compound

Rendimiento 53.8%

$CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1O$

(5Z,13E)-(8R,9R,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-5,13,18-prostatrienoic Acid Methylsulfonylamide

Rendimiento 53.8%

Reactantes

—

mixture

$CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](C/C=C\CCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1$

(5Z,13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid methylsulfonylamide

Reactivos

Ninguno

Disolventes

acetic acid water tetrahydrofuran

Condiciones de reacción

Condiciones detalladas

See reaction.notes.procedure_details.

Tratamiento posterior

1
OtroThe mixture was then evaporated under vacuum
2
Otrothe residue purified by column chromatography on silica gel with methylene chloride/5-30% isopropanol as the eluent

Procedimiento

156 mg of (5Z,13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-5,13,18-prostatrienoic acid methylsulfonylamide was stirred for 16 hours under argon at room temperature with 3 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was then evaporated under vacuum and the residue purified by column chromatography on silica gel with methylene chloride/5-30% isopropanol as the eluent, thus obtaining 62 mg of the desired compound.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US04444788uspto-grants-1984_04