Reaktion #1743263

ord-4af4b9280b3c402bbd0df32e2f6f05c1

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 ( 91 )
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 ( 92 )
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

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 ( 91 )
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 (91) (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 (92). Yield: 0.184 g (76%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05252605uspto-grants-1993_10