반응 #1506221

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trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid

triethylamine

diphenylphosphoryl azide

→

[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl]methylamine hydrochloride

용매

dimethylformamide

반응 조건

후처리

1. 1
   기타obtained in Reference Example 5
2. 2
   workup.ADDITIONto which was added dropwise
3. 3
   온도cooling
4. 4
   workup.STIRRINGThe reaction mixture was stirred for one hour at room temperature
5. 5
   추출The mixture was subjected to extraction with ether
6. 6
   세척The organic layer was washed with water
7. 7
   기타dried
8. 8
   농축which was then concentrated under reduced pressure
9. 9
   workup.DISSOLUTIONThe concentrate was dissolved in 100 ml of benzene
10. 10
    온도which was heated for 30 minutes
11. 11
    온도under reflux
12. 12
    농축The reaction mixture was concentrated under reduced pressure
13. 13
    workup.ADDITIONTo the concentrate was added 6 ml of conc. hydrochloric acid
14. 14
    온도the mixture was heated for one hour
15. 15
    온도under reflux
16. 16
    농축The reaction mixture was concentrated under reduced pressure
17. 17
    workup.ADDITIONby the addition of a 5% aqueous solution of potassium carbonate
18. 18
    추출followed by extraction with ethyl acetate
19. 19
    세척The organic layer was washed with water
20. 20
    기타dried
21. 21
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure
22. 22
    workup.ADDITIONTo the residue was added an ethanol solution of 4N hydrochloric acid

실험 절차

In 5 ml of dimethylformamide was dissolved 1.0 g of trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-acetic acid obtained in Reference Example 5. To the solution was added 0.3 ml of triethylamine, to which was added dropwise, while stirring under ice-cooling, 0.6 g of diphenylphosphoryl azide. The reaction mixture was stirred for one hour at room temperature, which was then poured into ice-water. The mixture was subjected to extraction with ether. The organic layer was washed with water and dried, which was then concentrated under reduced pressure. The concentrate was dissolved in 100 ml of benzene, which was heated for 30 minutes under reflux. The reaction mixture was concentrated under reduced pressure. To the concentrate was added 6 ml of conc. hydrochloric acid, and the mixture was heated for one hour under reflux. The reaction mixture was concentrated under reduced pressure. The concentrate was made alkaline by the addition of a 5% aqueous solution of potassium carbonate, followed by extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. To the residue was added an ethanol solution of 4N hydrochloric acid to lead it to hydrochloride to give 0.85 g of [trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepine-3-yl]methylamine hydrochloride as crystals, m.p. 245°-250° C.

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