Dichloromethane → Hydrochloric Acid

Participants

Reaction Steps

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 at room temperature, is added 0.72 g (0.0044 mole) of 1,1'-carbonyldiimidazole. After 2 days of stirring under room temperature, 2.6 g (0.02 mole) of 3-diethylaminopropylamine is added. The solution is allowed to stir at ambient temperature and is then 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 1.68 g of crude sticky solid. The solid is purified via flash chromatography twice to yield the free base. Treatment with ethanolic HCl yields two crops of (3β,5β,14β,17β)-14-Amino-3-[[[[3-(diethylamino)propyl]amino]carbonyl]oxy]androstane-17-carboxylic Acid, Methyl Ester Dihydrochloride Final Product.

Provenance & Evidence