Reaktion #3135

ord-77b94b1df1cb49efa2184366a550397e

Reaktionsgleichung

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide
→
CCCCC[C@H](O)/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O
N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamide
Ausbeute 87.2%

Edukte

F.c1ccncc1
hydrogen fluoride-pyridine
CCCCC[C@@H](/C=C/[C@@H]1C(SCCCCCC(=O)N(CC)CC)=C(OC(=O)CCC)C[C@H]1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C
N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide

Reagenzien

Keine

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

Using as the material and reagent a hydrogen fluoride-pyridine solution (0.2 ml) and N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-bis(tert-butyldimethylsiloxy)-7-thiaprosta-8,13-dienamide (169 mg), the same procedure as in Example 2 was performed to obtain N,N-diethyl(11R,12S,13E,15S)-9-butyryloxy-11,15-dihydroxy-7-thiaprosta-8,13-dienamide (101 mg, 78%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05731452uspto-grants-1998_03