Reaktion #47251

Reaktionsgleichung

1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol

2-t-butoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide

1-hydroxybenzotriazole

→

[1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-2-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid t-butyl ester

Ausbeute 93.2%

Lösungsmittel

dichloromethane

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was then stirred for 18 h at 25° C. under nitrogen
2. 2
   Waschenwashed with 2N aqueous hydrochloric acid, saturated sodium bicarbonate solution
3. 3
   Trocknena saturated sodium chloride solution and dried over magnesium sulfate
4. 4
   EinengenThe organic layer was concentrated

Vorschrift

A solution of 2-t-butoxycarbonylamino-3-(tetrahydro-pyran-4-yl)-propionic acid (500 mg, 1.83 mmol) in dichloromethane (15 mL) was treated with 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide (285 mg, 1.85 mmol) and 1-hydroxybenzotriazole (260 mg, 1.92 mmol). The reaction mixture was stirred at 25° C. for 2 h followed by the addition of 1-(3-amino-pyrazol-1-yl)-2-methyl-propan-2-ol (prepared in U.S. Pat. Appl. US2008021032 Example 80, 312 mg, 2.01 mmol). The reaction mixture was then stirred for 18 h at 25° C. under nitrogen. The reaction mixture was diluted with dichloromethane, washed with 2N aqueous hydrochloric acid, saturated sodium bicarbonate solution, a saturated sodium chloride solution and dried over magnesium sulfate. The organic layer was concentrated, to afford [1-[1-(2-hydroxy-2-methyl-propyl)-1H-pyrazol-3-ylcarbamoyl]-2-(tetrahydro-pyran-4-yl)-ethyl]-carbamic acid t-butyl ester (700 mg, 93%) as a white solid: LR-ES-MS m/z calculated for C20H34N4O5 [M]+ 410, observed [M+H]+ 411.

Quelle