반응 #3768

반응 방정식

β-thienyl-D,L-alanine

potassium carbonate

carbobenzyloxychloride

→

N-(Benzyloxycarbonyl) β-thienyl-D,L-alanine

수율 98.0%

desired compound

수율 98.0%

용매

H2O

water

dioxane

반응 조건

후처리

1. 1
   농축the reaction mixture was concentrated
2. 2
   기타The resultant layers were separated
3. 3
   세척the aqueous layer was washed with 75 mL of diethyl ether
4. 4
   workup.STIRRINGwith rapid stirring to pH=2.0
5. 5
   기타The layers were then separated
6. 6
   건조the organic layer was dried with sodium sulfate (Na2SO4)
7. 7
   여과filtered
8. 8
   농축concentrated

실험 절차

To a mixture of 3.0 g (16.9 mmol) of β-thienyl-D,L-alanine in 75 mL of water and 60 mL of dioxane, was added 5.6 g (40.6 mmol) of anhydrous potassium carbonate, followed by 2.85 mL (20 mmol) of carbobenzyloxychloride. The resulting mixture was stirred rapidly for approximately one hour. When the reaction was substantially complete, as indicated by thin layer chromatography (21/7/7/9, EtOAc/AcOH/CH3 CN/H2O), the reaction mixture was concentrated. The resultant layers were separated and the aqueous layer was washed with 75 mL of diethyl ether and then layered with 150 mL of methylene chloride. The resultant mixture was acidified with rapid stirring to pH=2.0 using 5N hydrochloric acid. The layers were then separated, and the organic layer was dried with sodium sulfate (Na2SO4), filtered and concentrated to provide 5.05 g of desired compound (98%).

출처