反応 #11687

反応方程式

(S)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt

5-chloroindole-2-carboxylic acid

1-hydroxy-7-azabenzotriazole

1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride

diisopropylethylamine

→

title compound

収率 88.8%

(S)-3-(5-chloroindole-2-carbonylamino)-2,3-dihydro-1,5-benzoxazepin-4(5H)-one

収率 88.8%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting yellow suspension was stirred for 30 min, during which a solution
2. 2
   その他formed
3. 3
   その他After evaporation under vacuum
4. 4
   workup.DISSOLUTIONthe residue was redissolved in ethyl acetate (50 mL)
5. 5
   洗浄the resulting solution was washed sequentially with 1.0 M aqueous hydrochloric acid (25 mL), 1.0 M aqueous sodium hydroxide (25 mL), water (25 mL) and brine (25 mL)
6. 6
   乾燥dried over anhydrous sodium sulfate
7. 7
   その他evaporated under vacuum
8. 8
   その他The resulting solid crude product was triturated with diethyl ether (20 mL three times)
9. 9
   その他by drying under vacuum

実験手順

Alternatively, to a mixture of (S)-3-amino-2,3-dihydro-1,5-benzoxazepin-4(5H)-one hydrochloride salt (54 mg) (prepared in Itoh, et al., Chem. Pharm. Bull. 1986, 34, 1128–1147), tetrahydrofuran (10 mL), 5-chloroindole-2-carboxylic acid (39 mg), 1-hydroxy-7-azabenzotriazole (31 mg), and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (57 mg) stirring at room temperature under argon was added diisopropylethylamine (65 mg). The resulting yellow suspension was stirred for 30 min, during which a solution formed. After evaporation under vacuum, the residue was redissolved in ethyl acetate (50 mL) and the resulting solution was washed sequentially with 1.0 M aqueous hydrochloric acid (25 mL), 1.0 M aqueous sodium hydroxide (25 mL), water (25 mL) and brine (25 mL), dried over anhydrous sodium sulfate, and evaporated under vacuum. The resulting solid crude product was triturated with diethyl ether (20 mL three times), followed by drying under vacuum to provide the title compound (63 mg).

出典