Reaktion #71111

Reaktionsgleichung

2-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-2H-[1,2,3]triazol-4-ylamine

N2

5-phenyl-oxazole-4-carboxylic acid

HOBt

EDC

→

title compound

5-Phenyl-oxazole-4-carboxylic acid (2-{2-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-2H-[1,2,3]triazol-4-yl)-amide

Lösungsmittel

CH2Cl2

CH2Cl2

water

CH2Cl2

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe resulting mixture was stirred at rt for 72 h
2. 2
   workup.ADDITIONwere added
3. 3
   Extraktionthe aqueous phase was extracted with CH2Cl2
4. 4
   WaschenThe combined organic phases were washed with water, brine
5. 5
   Trocknendried over MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent removed under reduced pressure

Vorschrift

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), a solution of 5-phenyl-oxazole-4-carboxylic acid (47 mg, 0.25 mmol) in CH2Cl2 (1.5 mL) was treated at rt with HOBt (40 mg, 0.30 mmol), EDC (119 mg, 0.62 mmol), DMAP (8 mg, 0.06 mmol) and the resulting mixture was stirred at rt for 30 min. 2-{2-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-oxazol-5-ylmethyl}-2H-[1,2,3]triazol-4-ylamine (80 mg, 0.25 mmol) in CH2Cl2 (1.0 mL) was then added and the resulting mixture was stirred at rt for 72 h. CH2Cl2 (20 mL) followed by water (15 mL) were added and the aqueous phase was extracted with CH2Cl2. The combined organic phases were washed with water, brine, dried over MgSO4, filtered, and the solvent removed under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=1.17 min, [M+H]+=495.54.

Quelle