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. After 2 days 2.74 g (0.02 mole) of S-2-phenylglycinol is dissolved in a minimum amount of CH2Cl2 and is added to the reaction mixture. The reaction mixture is heated at reflux for 4 days and another 0.54 g (0.004 mole) of (S)-2-phenylglycinol is added. The mixture is heated further at reflux temperature for 6 days. The solution is concentrated at reduced pressure and the residue is taken up with fresh CH2Cl2, is washed well with H2O until the washing is neutral. After drying over MgSO4, CH2Cl2 is removed under reduced pressure to yield the crude free base. The solid is purified by flash chromatography (5% MeOH/CH2Cl2, NH4OH) and then converted to its hydrochloride salt by the treatment with ethanolic HCl. Two crops of (3β(S),5β,14β,17β)-14-Amino-3-[[[(2-hydroxy-1-phenylethyl)amino]carbonyl]oxy]androstane-17-carboxylic Acid, Methyl Ester Hydrochloride Final Product are obtained.

1. additionis added to the reaction mixture
2. temperatureThe reaction mixture is heated
3. temperatureat reflux for 4 days
4. temperatureThe mixture is heated further
5. temperatureat reflux temperature for 6 days
6. concentrationThe solution is concentrated at reduced pressure
7. washis washed well with H2O until the washing
8. dry with materialAfter drying over MgSO4, CH2Cl2
9. customis removed under reduced pressure
10. customto yield the crude free base
11. customThe solid is purified by flash chromatography (5% MeOH/CH2Cl2, NH4OH)