반응 #5937

반응 방정식

(R)-3-(4-chlorophenyl)-1-[(S)-N-(2-naphthalenesulfonyl)prolyl]-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine

potassium hydroxide

→

(R)-(+)-3-(4-chlorophenyl)- 2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine

수율 63.1%

용매

ethanol water

반응 조건

후처리

1. 1
   온도is refluxed under argon for one hour
2. 2
   추출the mixture is extracted with ethyl acetate
3. 3
   세척The ethyl acetate layer is washed with water and saline
4. 4
   건조dried over sodium sulfate
5. 5
   workup.DISTILLATIONdistilled
6. 6
   기타to remove the solvent
7. 7
   기타The residue is purified by silica gel column chromatography (CHCl3)
8. 8
   기타recrystallized from ethyl acetate-hexane

실험 절차

A mixture of (R)-3-(4-chlorophenyl)-1-[(S)-N-(2-naphthalenesulfonyl)prolyl]-2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (11.50 g, 0.019 mole), 86 % potassium hydroxide (15.0 g, 0.227 mole) and ethanol-water (10:1, 230 ml) is refluxed under argon for one hour. The reaction mixture is poured into ice water and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water and saline, dried over sodium sulfate and distilled to remove the solvent. The residue is purified by silica gel column chromatography (CHCl3) and thereafter recrystallized from ethyl acetate-hexane to give (R)-(+)-3-(4-chlorophenyl)- 2,3-dihydro-1H-naphtho[2,1-b][1,4]thiazine (3.74 g, 63%). M.p. 205°-206° C.

출처