Reaktion #1367036

Reaktionsgleichung

2-(4-chlorophenoxy)-N′-hydroxyethanimidamide

(2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid

1,1′-carbonyldiimidazole

→

title compound

Ausbeute 48.5%

tert-Butyl (3R)-3-{3-[(4-chlorophenoxy)methyl]-1,2,4-oxadiazol-5-yl}-6-cyclohexylhexanoate

Ausbeute 48.5%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 17 hours
2. 2
   SonstigeThe solvent was removed under reduced pressure
3. 3
   Temperaturthe residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours
4. 4
   SonstigeThe crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1)

Vorschrift

A solution of (2R)-2-[2-(tert-butoxy)-2-oxoethyl]-5-cyclohexylpentanoic acid (Preparation 1) (300 mg, 1.00 mmol) in dichloromethane (15 ml) was treated with 1,1′-carbonyldiimidazole (162 mg, 1.00 mmol) and the solution was stirred at room temperature for 2 hours. 2-(4-chlorophenoxy)-N′-hydroxyethanimidamide (Patent US 97-815671 970313) (197 mg, 0.98 mmol) was then added and the mixture was stirred for 17 hours. The solvent was removed under reduced pressure and the residue was heated neat at 120° C. under a nitrogen atmosphere for 2 hours. The crude product was then purified by column chromatography on silica gel eluting with dichloromethane:methanol (99:1) to afford the title compound as a colourless oil (220 mg).

Quelle