Реакция #11687

Уравнение реакции

(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

Выход 88.8%

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

Выход 88.8%

Растворители

tetrahydrofuran

Условия реакции

Обработка

1. 1
   workup.STIRRINGThe resulting yellow suspension was stirred for 30 min, during which a solution
2. 2
   Другоеformed
3. 3
   ДругоеAfter evaporation under vacuum
4. 4
   workup.DISSOLUTIONthe residue was redissolved in ethyl acetate (50 mL)
5. 5
   Промывкаthe 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
   Сушкаdried over anhydrous sodium sulfate
7. 7
   Другоеevaporated under vacuum
8. 8
   ДругоеThe resulting solid crude product was triturated with diethyl ether (20 mL three times)
9. 9
   Другоеby drying under vacuum

Методика

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).

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