تفاعل #413368

ord-804c7cee460943a3b388ee37f0c1ecea

معادلة التفاعل

CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](CCCCCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1
(13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-13,18-prostadienoic acid methylsulfonylamide
→
CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](CCCCCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1O
title compound
المردود 45.0%
CC(C)=CCC(C)[C@H](O)/C=C/[C@@H]1[C@@H](CCCCCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1O
(13E)-(8R,9R,11R,12R,15S,16RS)-9-Chloro-11,15-dihydroxy-16,19-dimethyl-13,18-prostadienoic Acid Methylsulfonylamide
المردود 45.0%

المتفاعلات

—
mixture
CC(C)=CCC(C)[C@@H](/C=C/[C@@H]1[C@@H](CCCCCCC(=O)NS(C)(=O)=O)[C@H](Cl)C[C@H]1OC1CCCCO1)OC1CCCCO1
(13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-13,18-prostadienoic acid methylsulfonylamide

الكواشف

لا شيء

المذيبات

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

ظروف التفاعل

الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

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

الإجراء التجريبي

103 mg of (13E)-(8R,9R,11R,12R,15S,16RS)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,19-dimethyl-13,18-prostadienoic acid methylsulfonylamide was stirred for 24.5 hours under argon at room temperature with 1.9 ml of a mixture of acetic acid/water/tetrahydrofuran (65/35/10). Then the mixture was concentrated under vacuum and the residue purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent, thus obtaining 34.3 mg of the title compound.

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US04444788uspto-grants-1984_04