反应详情

(4R-cis)-1,1-dimethylethyl 6-[2[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-1H-pyrrol-1-yl]ethyl]-2,2-dimethyl-1,3-dioxane-4-acetate, 4.37 g (6.68 mol), is dissolved in 200 mL of tetrahydrofuran and 15 mL of 10% hydrochloric acid solution is added, and the solution is stirred for 15 hours. To this solution is added sodium hydroxide (3.6 g) and the mixture is stirred for 30 hours. The reaction is stopped by adding 150 mL of water, 90 mL of hexane, and separating the layers. The aqueous layer is acidified with dilute hydrochloric acid solution, stirred for three hours and extracted with 150 mL of ethyl acetate. A drop of concentrated hydrochloric acid is added to the ethyl acetate solution and the solution is allowed to stand 18 hours. The solution is concentrated in vacuo and the concentrate is redissolved in 50 mL of ethyl acetate and treated with one drop of concentrated hydrochloric acid. The solution is stirred two hours, concentrated in vacuo, and dissolved in 3.0 mL of toluene. (2R-trans)-5-(4-fluorophenyl)-2-(1-methylethyl)-N,4-diphenyl-1-[2-(tetrahydro-4-hydroxy-6-oxo2H-pyran-2-yl)ethyl]-1H-pyrrole-3-carboxamide (3.01 g) is isolated in two crops.

1. stirringthe mixture is stirred for 30 hours
2. customseparating the layers
3. stirringstirred for three hours
4. extractionextracted with 150 mL of ethyl acetate
5. additionA drop of concentrated hydrochloric acid is added to the ethyl acetate solution
6. waitto stand 18 hours
7. concentrationThe solution is concentrated in vacuo
8. dissolutionthe concentrate is redissolved in 50 mL of ethyl acetate
9. additiontreated with one drop of concentrated hydrochloric acid
10. stirringThe solution is stirred two hours
11. concentrationconcentrated in vacuo
12. dissolutiondissolved in 3.0 mL of toluene