反応 #10386

反応方程式

4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2,5-difluorobenzoic acid ethyl ester

cyclopropylamine

dimethyl sulfoxide

→

title compound

収率 43.2%

4-[(S)-3-tert-Butoxycarbonylaminopyrrolidin-1-yl]-3-chloro-2-cyclopropylamino-5-fluorobenzoic acid ethyl ester

収率 43.2%

溶媒

ethyl acetate

反応条件

後処理

1. 1
   洗浄washed with saturated NaHCO3, water, and brine
2. 2
   乾燥The organic layer is dried over MgSO4
3. 3
   ろ過filtered
4. 4
   濃縮the filtrate is concentrated
5. 5
   その他to afford a brown residue
6. 6
   その他The residue is then purified via flash column chromatography (1:1 ethyl acetate/hexanes)

実験手順

A solution of 4-[(S)-3-(tert-butoxycarbonylamino)pyrrolidin-1-yl]-3-chloro-2,5-difluorobenzoic acid ethyl ester (Example 2c, 9.34 g, 23.1 mmol), cyclopropylamine (16 mL, 228 mmol), and dimethyl sulfoxide (30 mL) is heated in a sealed tube at 110° C. for 3 days. After cooling to room temperature, the reaction mixture is diluted with ethyl acetate and washed with saturated NaHCO3, water, and brine. The organic layer is dried over MgSO4, filtered, and the filtrate is concentrated to afford a brown residue. The residue is then purified via flash column chromatography (1:1 ethyl acetate/hexanes) to afford the title compound (4.41 g). MS CI: m/z 442 (MH+).

出典