Reacción #413372

ord-416380856dfb4db09b21bb817c4cc65a

Ecuación de reacción

CC(=O)NC(=O)CCCCCC[C@@H]1[C@@H](/C=C/[C@@H](CCC=C(C)C)OC2CCCCO2)[C@H](OC2CCCCO2)C[C@H]1Cl
(13E)-(8R,9R,11R,12R,15R)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-19-methyl-13,18-prostadienoic acid acetylamide
→
CC(=O)NC(=O)CCCCCC[C@@H]1[C@@H](/C=C/[C@@H](O)CCC=C(C)C)[C@H](O)C[C@H]1Cl
title compound
Rendimiento 59.7%
CC(=O)NC(=O)CCCCCC[C@@H]1[C@@H](/C=C/[C@@H](O)CCC=C(C)C)[C@H](O)C[C@H]1Cl
(13E)-(8R,9R,11R,12R,15S)-9-Chloro-11,15-dihydroxy-19-methyl-13,18-prostadienoic Acid Acetylamide
Rendimiento 59.7%

Reactantes

—
mixture
CC(=O)NC(=O)CCCCCC[C@@H]1[C@@H](/C=C/[C@@H](CCC=C(C)C)OC2CCCCO2)[C@H](OC2CCCCO2)C[C@H]1Cl
(13E)-(8R,9R,11R,12R,15R)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-19-methyl-13,18-prostadienoic acid acetylamide

Reactivos

Ninguno

Disolventes

C1CCOC1.CC(=O)O.O
acetic acid water tetrahydrofuran

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    ConcentraciónThe mixture was then concentrated under vacuum
  2. 2
    Otrothe residue was purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent

Procedimiento

460 mg of (13E)-(8R,9R,11R,12R,15R)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-19-methyl-13,18-prostadienoic acid acetylamide was stirred under argon at room temperature for 17 hours with 10 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). The mixture was then concentrated under vacuum, and the residue was purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent, thus obtaining 197 mg of the title compound.

Fuente

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