تفاعل #413374

ord-b148c02143204c9587fc001ee5f3a181

معادلة التفاعل

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

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

→

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

title compound

المردود 59.1%

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

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

المردود 59.1%

المتفاعلات

—

mixture

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

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

الكواشف

لا شيء

المذيبات

acetic acid water tetrahydrofuran

ظروف التفاعل

الظروف التفصيلية

See reaction.notes.procedure_details.

المعالجة

1
أخرىThe mixture was then evaporated under vacuum
2
أخرىthe residue purified by column chromatography on silica gel with hexane/20-80% ethyl acetate

الإجراء التجريبي

Under argon, 427 mg of (5Z,13E,18Z)-(8R,9R,11R,12R,15S,16RS)-9,19-dichloro-16-methyl-11,15-bis(tetrahydropyran-2-yloxy)-5,13,18-prostatrienoic acid was stirred at room temperature for 16 hours with 9 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 hexane/20-80% ethyl acetate, thus producing 180 mg of the title compound.

المصدر

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