反応 #5934

反応方程式

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

収率 51.5%

溶媒

pyridine

反応条件

後処理

1. 1
   洗浄the mixture is washed with 5 % hydrochloric acid, water, aqueous sodium hydrogen carbonate solution, water and saline in this order
2. 2
   その他the ethyl acetate layer is separated
3. 3
   乾燥dried over sodium sulfate
4. 4
   workup.DISTILLATIONdistilled
5. 5
   その他to remove the solvent
6. 6
   洗浄From the fraction eluted first there

実験手順

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.

出典