Dichloromethane → Hydrochloric Acid
Reaction equation
[NH2:1][C@@:2]12[C@H:19]3[C@@H:10]([C@:11]4([CH3:21])[C@H:16]([CH2:17][CH2:18]3)[CH2:15][C@@H:14]([OH:20])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C@:6]1([CH3:7])[C@@H:5]([C:22]([O:24][CH3:25])=[O:23])[CH2:4][CH2:3]2.[C:26](N1C=CN=C1)(N1C=CN=C1)=[O:27].[NH2:38][CH2:39][CH:40]([OH:47])[CH2:41][N:42]([CH2:45][CH3:46])[CH2:43][CH3:44].C(Cl)[Cl:49]>>[ClH:49].[ClH:49].[ClH:49].[NH2:1][C@@:2]12[C@H:19]3[C@@H:10]([C@:11]4([CH3:21])[C@H:16]([CH2:17][CH2:18]3)[CH2:15][C@@H:14]([O:20][C:26]([NH:38][CH2:39][CH:40]([OH:47])[CH2:41][N:42]([CH2:45][CH3:46])[CH2:43][CH3:44])=[O:27])[CH2:13][CH2:12]4)[CH2:9][CH2:8][C@:6]1([CH3:7])[C@@H:5]([C:22]([O:24][CH3:25])=[O:23])[CH2:4][CH2:3]2Participants
Procedure
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 40 ml of CH2Cl2 under N2 at room temperature under stirring is added 0.72 g (0.0044 mole) of 1,1'-carbonyldiimidazole. After 2 days, 2.92 g (0.02 mole) of 1-amino-3-diethylamino-2-propanol is added. The solution turned somewhat cloudy. After 3 days of stirring under N2 at room temperature, the mixture is worked up the same way as in Example 8. The crude solid (1.8 g) is purified by flash chromatography (5% MeOH/CH2Cl2, NH4OH) to yield a sticky solid. Treatment with ethanolic HCl yields (3β,5β,14β,17β)-14-Amino-3-[[[(3-diethylamino-2-hydroxypropyl)amino]carbonyl]oxy]androstane-17-carboxylic Acid, Methyl Ester Dihydrochloride Final Product.
Workup
- customThe crude solid (1.8 g) is purified by flash chromatography (5% MeOH/CH2Cl2, NH4OH)
- customto yield a sticky solid
Sources & evidence
- ORD record
- ord-7f63d30ed837456b9736bbb8135e3519
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05922703
Reaction notes
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