反应详情

To a solution of 1.4 g (0.004 mole) of (3β,5β,14β,17β)-14-Amino-3-hydroxyandrostane-17-carboxylic Acid, Methyl Ester, prepared according to the procedure described in U.S. Pat. No. 4,885,280, incorporated by reference herein, in 50 ml of CH2Cl2 under N2 and stirring, is added 0.72 g (0.0044 mole) of 1,1'-carbonyldiimidazole. The mixture is allowed to stir for 2 days, then 2.24 g (0.02 mole) of N,N-diethylethylenediamine is added. After 48 hr of stirring, the solution is concentrated and the residue is taken up with fresh CH2Cl2 and is washed well with water until the washing is neutral. After drying over MgSO4, CH2Cl2 is removed under reduced pressure to yield 1.55 g of crude free base. Purification via flash chromatography using 3% MeOH/CH2Cl2 (NH4OH) at first, followed by 4% and then 7% MeOH/CH2Cl2 provides the free base. Treatment with ethanolic HCl yields the analytically pure (3β,5β,14β,17β)-14-Amino-3-[[[[2-(diethylamino)ethyl]amino]carbonyl]oxy]androstane-17-carboxylic Acid, Methyl Ester Dihydrochloride Final Product.

1. stirringAfter 48 hr of stirring
2. concentrationthe solution is concentrated
3. washis washed well with water until the washing
4. dry with materialAfter drying over MgSO4, CH2Cl2
5. customis removed under reduced pressure
6. customto yield 1.55 g of crude free base
7. customPurification via flash chromatography
8. custom7% MeOH/CH2Cl2 provides the free base