Reaktion #158435

Reaktionsgleichung

TBAF

4-(6-phenyl-1,4-dioxaspiro[4.5]decan-6-yl)butanoic acid

(R,Z)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N′-hydroxy-3,5-dimethylbenzimidamide

N,N′-diisopropylcarbodiimide

→

3-(4-(((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3,5-dimethylphenyl)-5-(3-(6-phenyl-1,4-dioxaspiro[4.5]decan-6-yl)propyl)-1,2,4-oxadiazole

Ausbeute 59.6%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred at room temp for 18 hrs
2. 2
   SonstigeIt was partitioned between EtOAc and water
3. 3
   Extraktionthe aqueous layer was extracted with EtOAc once more
4. 4
   WaschenCombined extracts were washed with Na2SO4
5. 5
   Sonstigeevaporated
6. 6
   Sonstigeto give an oily residue
7. 7
   SonstigeIt was purified by Combiflash (24 g silica gel)
8. 8
   Wascheneluting with 3:7

Vorschrift

To a solution of 4-(6-phenyl-1,4-dioxaspiro[4.5]decan-6-yl)butanoic acid (62.0 mg, 0.204 mmol) and (R,Z)-4-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-N′-hydroxy-3,5-dimethylbenzimidamide (50 mg, 0.17 mmol) in acetonitrile (2 mL) was added N,N′-diisopropylcarbodiimide (0.032 mL, 0.204 mmol), and the mixture was stirred for 1 hr at room temp. Then 1M TBAF (0.221 mL, 0.221 mmol) was added, and the mixture was stirred at room temp for 18 hrs. It was partitioned between EtOAc and water, and the aqueous layer was extracted with EtOAc once more. Combined extracts were washed with Na2SO4 and evaporated to give an oily residue. It was purified by Combiflash (24 g silica gel) eluting with 3:7 followed by 1:1 EtOAc-hexane to give 3-(4-(((R)-2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)-3,5-dimethylphenyl)-5-(3-(6-phenyl-1,4-dioxaspiro[4.5]decan-6-yl)propyl)-1,2,4-oxadiazole as an oil (57 mg). LC/MS: m/e 563.21 (M+H)+.

Quelle