Reaktion #336299

ord-c56e241a7335481e88cb607492b19b22

Reaktionsgleichung

CC(=O)O
acetic acid
CCCCC(F)(F)C(=O)CC[C@H]1[C@H](OC2CCCCO2)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
compound ( 59 )
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
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 ( 60 )
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

—
resultant mixture
CC(=O)O
acetic acid
CCCCC(F)(F)C(=O)CC[C@H]1[C@H](OC2CCCCO2)CC(=O)[C@@H]1CCCCCCCCC(=O)OC(C)C
compound ( 59 )
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
O
water

Reagenzien

Keine

Lösungsmittel

C1CCOC1
THF
—
solvent

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe obtained crude product

Vorschrift

The compound (59) (0.288 g) was dissolved in a mixed solvent (30 ml) consisting of acetic acid, water and THF (4:2:1) and the solution was kept at 45° C. for 3.5 hours. The resultant mixture was worked up with the conventional procedure and the obtained crude product was subjected to silicagel column chromatography to give the titled compound (60) Yield: 0.184 g (76%).

Quelle

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