Reaktion #336298

ord-49794275145f41d69a90b204d478251b

Reaktionsgleichung

$CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)OCC(=O)c1ccccc1$

compound ( 46 )

$CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)OCC(=O)c1ccccc1$

phenacyl (Z)-9-(1R)-[(2R,3R)-2-{4,4-difluoro-3-oxooctyl}-3-hydroxy-5-oxocyclopentyl}-7-nonenoate

→

$CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)O$

titled compound ( 57 )

$CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)O$

(Z)-9-(1R)-[(2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]-7-nonenoic acid

Edukte

$CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)OCC(=O)c1ccccc1$

compound ( 46 )

$CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1C/C=C\CCCCCC(=O)OCC(=O)c1ccccc1$

phenacyl (Z)-9-(1R)-[(2R,3R)-2-{4,4-difluoro-3-oxooctyl}-3-hydroxy-5-oxocyclopentyl}-7-nonenoate

—

resultant mixture

Reagenzien

zinc

Lösungsmittel

acetic acid

Reaktionsbedingungen

Detaillierte Bedingungen

See reaction.notes.procedure_details.

Aufarbeitung

1
workup.ADDITIONadded in portions at the room temperature for 2.5 hours

Vorschrift

A solution of the compound (46) (0.272 g) in acetic acid (10 ml) was treated with zinc (3.5 g) added in portions at the room temperature for 2.5 hours. The resultant mixture was worked up with the conventional procedure and the residue was subjected to silicagel column chromatography to give the titled compound (57). Yield: 0.177 g (81%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05212324uspto-grants-1993_05