Réaction #3126

ord-947e00ce913b48258528de610493e045

Équation de réaction

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](C[C@H](C)CCCC)O[Si](C)(C)C(C)(C)C
butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate
→
CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O)[C@@H]1/C=C/[C@@H](O)C[C@H](C)CCCC
butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate
Rendement 72.0%

Réactifs

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCOC(=O)CCCCCSC1=C(OC(=O)CCC)C[C@@H](O[Si](C)(C)C(C)(C)C)[C@@H]1/C=C/[C@H](C[C@H](C)CCCC)O[Si](C)(C)C(C)(C)C
butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Mode opératoire

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-17,20-dimethyl-7-thiaprosta-8,13-dienoate (138 mg), the same procedure as in Example 2 was performed to obtain butyl (11R,12S,13E,15S,17R)-9-butyryloxy-11,15-dihydroxy-17,20-dimethyl-7-thiaprosta-8,13-dienoate (69 mg, 72%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US05731452uspto-grants-1998_03