تفاعل #5937

معادلة التفاعل

(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

المردود 63.1%

المذيبات

ethanol water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةis refluxed under argon for one hour
2. 2
   استخلاصthe mixture is extracted with ethyl acetate
3. 3
   غسيلThe ethyl acetate layer is washed with water and saline
4. 4
   تجفيفdried over sodium sulfate
5. 5
   workup.DISTILLATIONdistilled
6. 6
   أخرىto remove the solvent
7. 7
   أخرىThe residue is purified by silica gel column chromatography (CHCl3)
8. 8
   أخرىrecrystallized from ethyl acetate-hexane

الإجراء التجريبي

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.

المصدر