反応 #1270359

反応方程式

(S)-3-{[1-(2-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carbonyl]-amino}-3-(2-methyl-phenyl)-propionic acid ethyl ester

1-(2-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid

ethyl (S)-3-amino-3-(2-methyl-phenyl)-propionate

cesium carbonate

3-bromomethyl-3-methyl-oxetane

→

(S)-3-{[1-(2-Fluoro-phenyl)-5-(3-methyl-oxetan-3-ylmethoxy)-1H-pyrazole-3-carbonyl]-amino}-3-(2-methyl-phenyl)-propionic acid ethyl ester

溶媒

DMF

反応条件

後処理

1. 1
   その他as described in synthesis example 2)
2. 2
   その他After evaporation of the solvent the residue
3. 3
   その他After removal of the solvent from the organic phase 100 mg (82%) of the product
4. 4
   その他are obtained

実験手順

101 mg (0.245 mmol) of (S)-3-{[1-(2-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carbonyl]-amino}-3-(2-methyl-phenyl)-propionic acid ethyl ester (prepared from 1-(2-fluoro-phenyl)-5-hydroxy-1H-pyrazole-3-carboxylic acid and ethyl (S)-3-amino-3-(2-methyl-phenyl)-propionate analogously as described in synthesis example 2) were dissolved in 3 ml of DMF, and 160 mg (0.5 mmol) of cesium carbonate and 41.3 mg (0.245 mmol) of 3-bromomethyl-3-methyl-oxetane were added. The mixture was stirred for 4 h at 65° C. After evaporation of the solvent the residue was subjected to an aqueous work-up with EA and 10% aqueous solution of citric acid. After removal of the solvent from the organic phase 100 mg (82%) of the product are obtained.

出典