反応 #5937

反応方程式

(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

収率 63.1%

溶媒

ethanol water

反応条件

後処理

1. 1
   温度is refluxed under argon for one hour
2. 2
   抽出the mixture is extracted with ethyl acetate
3. 3
   洗浄The ethyl acetate layer is washed with water and saline
4. 4
   乾燥dried over sodium sulfate
5. 5
   workup.DISTILLATIONdistilled
6. 6
   その他to remove the solvent
7. 7
   その他The residue is purified by silica gel column chromatography (CHCl3)
8. 8
   その他recrystallized from ethyl acetate-hexane

実験手順

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.

出典