Reaktion #1368390

ord-98145c7c3ae046bf8fcf94214b9cb959

Reaktionsgleichung

CCCCC(F)(F)C(=O)CC[C@H]1[C@H](OC2CCCCO2)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
compound ( 19-a )
CCCCC(F)(F)C(=O)CC[C@H]1[C@H](OC2CCCCO2)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
isopropyl 9-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(tetrahydropyranyloxy)cyclopentyl]-nonanoate
CC(=O)O
acetic acid
O
water
→
CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
titled compound ( 20-a )
Ausbeute 76.0%
CCCCC(F)(F)C(=O)CC[C@H]1[C@H](O)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
isopropyl 9-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-3-hydroxy-5-oxocyclopentyl]nonanoate
Ausbeute 76.0%

Edukte

CCCCC(F)(F)C(=O)CC[C@H]1[C@H](OC2CCCCO2)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
compound ( 19-a )
CCCCC(F)(F)C(=O)CC[C@H]1[C@H](OC2CCCCO2)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
isopropyl 9-[(1R,2R,3R)-2-(4,4-difluoro-3-oxooctyl)-5-oxo-3-(tetrahydropyranyloxy)cyclopentyl]-nonanoate
CC(=O)O
acetic acid
O
water

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF

Reaktionsbedingungen

Temperatur
45°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe crude product obtained by the conventional treatment of the reaction mixture
  2. 2
    Sonstigewas purified on silica gel column

Vorschrift

The compound (19-a)(0.288 g) was dissolved in the solvent mixture (acetic acid:water:THF=4:2:1)(30 ml), and the solution was maintained at 45° C. for 3.5 hours. The crude product obtained by the conventional treatment of the reaction mixture was purified on silica gel column to give the titled compound (20-a) [yield:0.184 g(76%)].

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06452039B1uspto-grants-2002_09