反応 #413370

ord-23eb6be0bfc341818c7b1007c63019a1

反応方程式

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

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

→

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

title compound

収率 51.4%

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

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

収率 51.4%

反応物

—

mixture

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

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

試薬

なし

溶媒

acetic acid water tetrahydrofuran

反応条件

詳細条件

See reaction.notes.procedure_details.

後処理

1
その他The mixture was then evaporated under vacuum
2
その他the residue purified by column chromatography on silica gel with hexane/0-100% ethyl acetate as the eluent

実験手順

1.04 g of (5Z,13E)-(8R,9R,11R,12R,15R)-9-chloro-11,15-bis(tetrahydropyran-2-yloxy)-16,16,19-trimethyl-5,13,18-prostatrienoic acid was stirred under argon at room temperature for 19 hours with 21 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/0-100% ethyl acetate as the eluent, thus obtaining 380 mg of the title compound.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US04444788uspto-grants-1984_04