تفاعل #11687

معادلة التفاعل

(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

المردود 88.8%

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

المردود 88.8%

المذيبات

tetrahydrofuran

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGThe resulting yellow suspension was stirred for 30 min, during which a solution
2. 2
   أخرىformed
3. 3
   أخرىAfter evaporation under vacuum
4. 4
   workup.DISSOLUTIONthe residue was redissolved in ethyl acetate (50 mL)
5. 5
   غسيلthe 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
   تجفيفdried over anhydrous sodium sulfate
7. 7
   أخرىevaporated under vacuum
8. 8
   أخرىThe resulting solid crude product was triturated with diethyl ether (20 mL three times)
9. 9
   أخرىby drying under vacuum

الإجراء التجريبي

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).

المصدر