Reacción #413363

ord-8edd289791b643e784bb05f2b78fda17

Ecuación de reacción

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

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

→

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

title compound

Rendimiento 14.6%

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

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

Rendimiento 14.6%

Reactantes

—

mixture

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

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

Reactivos

Ninguno

Disolventes

acetic acid water tetrahydrofuran

Condiciones de reacción

Condiciones detalladas

See reaction.notes.procedure_details.

Tratamiento posterior

1
OtroThe mixture was evaporated
2
Otrounder vacuum and the residue purified by column chromatography on silanized silica gel with ethanol/water (1:1)

Procedimiento

Under argon, 915 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 was stirred at room temperature for 17 hours with 19 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was evaporated thereafter under vacuum and the residue purified by column chromatography on silanized silica gel with ethanol/water (1:1), thus obtaining 94 mg of the title compound.

Fuente

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