반응 #11687

반응 방정식

(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

수율 88.8%

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

수율 88.8%

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   workup.STIRRINGThe resulting yellow suspension was stirred for 30 min, during which a solution
2. 2
   기타formed
3. 3
   기타After evaporation under vacuum
4. 4
   workup.DISSOLUTIONthe residue was redissolved in ethyl acetate (50 mL)
5. 5
   세척the 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
   건조dried over anhydrous sodium sulfate
7. 7
   기타evaporated under vacuum
8. 8
   기타The resulting solid crude product was triturated with diethyl ether (20 mL three times)
9. 9
   기타by drying under vacuum

실험 절차

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).

출처