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HRID14377

反应详情

EQUATION

反应方程式

HRID 14377 的结构方程式

REACTANTS

反应物

1
结构：CC(=O)OCC(=O)[C@@]1(OC(=O)N[C@H](C)c2ccccc2)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C
HCID86603938

未命名化合物

PRODUCTS

生成物

1
结构：C[C@@H](NC(=O)O[C@]1(C(=O)CO)[C@@H](C)C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@]4(C)[C@@]3(F)[C@@H](O)C[C@@]21C)c1ccccc1
HCID44587250

未命名化合物

收率 57.9%

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CO.ClC(Cl)Cl
溶剂HCID21584188

Chloroform methanol

C2H5Cl3O

PROCEDURE

实验过程

(11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate (42 mg, 0.064 mmol) was dissolved in 1.25 mL of a pre-mixed solution of methanol/chloroform/6N HCl (10:2:1) and stirred at room temperature for 24.5 hours. The solution was then partitioned between ethyl acetate and water and the organic phase was washed with water (twice) and brine and dried over Na2SO4. Filtration and evaporation under vacuum gave a white film which was purified by preparative thin layer chromatography on silica gel, eluting with ethyl acetate/hexane/dichloromethane/methanol (95:95:95:15), to yield 20 mg of (11β,16β)-9-fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl (1R)-1-phenylethylcarbamate as a white solid.

WORKUP

后处理

  1. customThe solution was then partitioned between ethyl acetate and water
  2. washthe organic phase was washed with water (twice) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationFiltration and evaporation under vacuum
  5. customgave a white film which
  6. customwas purified by preparative thin layer chromatography on silica gel
  7. washeluting with ethyl acetate/hexane/dichloromethane/methanol (95:95:95:15)