반응 #1194239

반응 방정식

p-(carbamoylmethyl)phenoxy-2,3-epoxypropane

isopropylamine

→

(S)-atenolol

수율 70.2%

용매

methanol

반응 조건

후처리

1. 1
   온도the reaction temperature was raised to room temperature
2. 2
   기타After the reaction
3. 3
   기타condensed in vacuo until crystals
4. 4
   기타to separate
5. 5
   온도cooled
6. 6
   여과filtrated by suction
7. 7
   기타dried in vacuo

실험 절차

P-Hydroxyphenylacetamide (1 g) and (S)-glycidyl p-toluenesulfonate (1.51 g, 99.3% e.e.) were dissolved in acetone (30 ml). Potassium carbonate (1.19 g) was added to the solution and stirred for 30 hours under refluxing. After the reaction, inorganic materials were filtered off and acetone was removed to give 1.43 g of crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane. Then, crude (S)-1-[p-(carbamoylmethyl)phenoxy-2,3-epoxypropane (1.43 g) was dissolved in methanol (8 ml). The solution was dropped in isopropylamine (6.8 g) under cooling to 10° C. over a period of 1 hour and the reaction temperature was raised to room temperature and stirred for 7 hours. After the reaction, the mixture was condensed in vacuo until crystals beginning to separate, cooled, filtrated by suction and dried in vacuo to give crude (S)-atenolol (1.29 g). The optical purity of it was 62.8% e.e. by measurement of Chiral column OD (Daisel Chemical industries Ltd.).

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