반응 #483889

반응 방정식

5-acetyl-2-((2-azidoethyl)oxy)methyl-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(3,4-methylenedioxy)phenylpyridine

NaOH

dioxane

→

title compound

수율 25.0%

5-Acetyl-2-((2-azidoethyl)oxy)methyl-1,4-dihydro-6-methyl-4-(3,4-methylenedioxy)phenylpyridine-3-carboxylic Acid

수율 25.0%

반응 조건

후처리

1. 1
   기타obtained from the previous experiment (340 mg and 200 mg)
2. 2
   기타after completion of the reaction
3. 3
   농축The two batches were concentrated in vacuo
4. 4
   workup.DISSOLUTIONthe combined batches were dissolved in 40 mL of water
5. 5
   세척washed with dichloromethane (30 mL) and EtOAc (20 mL)
6. 6
   추출extracted with dichloromethane (2×50 mL)
7. 7
   세척The combined dichloromethane extracts were washed with brine (40 mL)
8. 8
   건조dried (MgSO4)
9. 9
   기타the solvent was removed in vacuo

실험 절차

This product was obtained from deprotection of two batches of 5-acetyl-2-((2-azidoethyl)oxy)methyl-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(3,4-methylenedioxy)phenylpyridine obtained from the previous experiment (340 mg and 200 mg) and were combined after completion of the reaction. A mixture of 5-acetyl-2-((2-azidoethyl)oxy)methyl-3-(2-cyanoethoxy)carbonyl-1,4-dihydro-6-methyl-4-(3,4-methylenedioxy)phenylpyridine (340 mg, 0.750 mmol; 200 mg (60%), 0.200 mmol), 1 N NaOH (1.12 mL; 0.40 mL) in a mixture of dioxane (3 mL; 3 mL) were stirred at room temperature for 1.5 hours. The two batches were concentrated in vacuo, the combined batches were dissolved in 40 mL of water, washed with dichloromethane (30 mL) and EtOAc (20 mL), acidified with 1 N HCl solution (pH=4-5), and extracted with dichloromethane (2×50 mL). The combined dichloromethane extracts were washed with brine (40 mL), dried (MgSO4), and the solvent was removed in vacuo to give 300 mg (25%) of the title compound as a yellow paste which solidified on standing: mp 120° C. (decomp.). The product was used in the next step after spectral characterization.

출처