반응 #5934

반응 방정식

ethyl acetate

(±)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine

(S)-N-(2-naphthalenesulfonyl)prolyl chloride

→

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

수율 51.5%

용매

pyridine

반응 조건

후처리

1. 1
   세척the mixture is washed with 5 % hydrochloric acid, water, aqueous sodium hydrogen carbonate solution, water and saline in this order
2. 2
   기타the ethyl acetate layer is separated
3. 3
   건조dried over sodium sulfate
4. 4
   workup.DISTILLATIONdistilled
5. 5
   기타to remove the solvent
6. 6
   세척From the fraction eluted first there

실험 절차

To a solution of (±)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (10.01 g, 0.038 mole) in pyridine (150 ml) is added (S)-N-(2-naphthalenesulfonyl)prolyl chloride (18.57 g, 0.057 mole), and the mixture is stirred at room temperature for 4 hours. To the reaction mixture is added ethyl acetate, and the mixture is washed with 5 % hydrochloric acid, water, aqueous sodium hydrogen carbonate solution, water and saline in this order, and the ethyl acetate layer is separated, dried over sodium sulfate and distilled to remove the solvent. The resulting caramel is subjected to silica gel column chromatography (hexane:ethyl acetate=5:1 - 3:1). From the fraction eluted first there is obtained (R)-2-(4-chlorophenyl)-4-[(S)-N-(2-naphthalenesulfonyl)prolyl]-3,4-dihydro-2H-1,4-benzothiazine (10.75 g, 51 %) as crystals. M.p. 147°-151° C.

출처