Reaktion #1879

Reaktionsgleichung

N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]glycine

acetic anhydride

triethylamine

→

N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]-N-acetyl glycine

Lösungsmittel

methanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was heated for one hour
2. 2
   Temperaturunder reflux
3. 3
   EinengenThe reaction mixture was concentrated under reduced pressure, which
4. 4
   Extraktionwas subjected to extraction with ethyl acetate
5. 5
   WaschenThe organic layer was washed with an aqueous solution of potassium hydrogensulfate
6. 6
   Trocknenan aqueous solution of sodium hydrogencarbonate and water, which was then dried
7. 7
   workup.DISTILLATIONby distilling off the solvent
8. 8
   workup.DISSOLUTIONThe residue was dissolved in 4 ml of methanol, to which
9. 9
   workup.ADDITIONwas added 2 ml of a 5% aqueous solution of potassium carbonate
10. 10
    workup.STIRRINGThe mixture was stirred for 30 minutes at 60° C
11. 11
    EinengenThe reaction mixture was concentrated under reduced pressure, to which
12. 12
    workup.ADDITIONwas added 1N hydrochloric acid
13. 13
    Extraktionfollowed by extraction with ethyl acetate
14. 14
    WaschenThe organic layer was washed with water
15. 15
    Sonstigedried
16. 16
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

In 4 ml of methanol was dissolved 60 mg of ethyl ester of N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]glycine obtained in Example 40. To the solution were added 0.2 ml of acetic anhydride and 0.2 ml of triethylamine. The mixture was heated for one hour under reflux while stirring. The reaction mixture was concentrated under reduced pressure, which was subjected to extraction with ethyl acetate. The organic layer was washed with an aqueous solution of potassium hydrogensulfate, an aqueous solution of sodium hydrogencarbonate and water, which was then dried, followed by distilling off the solvent. The residue was dissolved in 4 ml of methanol, to which was added 2 ml of a 5% aqueous solution of potassium carbonate. The mixture was stirred for 30 minutes at 60° C. The reaction mixture was concentrated under reduced pressure, to which was added 1N hydrochloric acid to acidify the solution, followed by extraction with ethyl acetate. The organic layer was washed with water and dried, then the solvent was distilled off under reduced pressure. From the residue, 45 mg of N-[trans-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-ylmethyl]-N-acetyl glycine was obtained as crystals, m.p. 143°-145° C.

Quelle