Dichloromethane → Hydrochloric Acid

HRID 581713Notes

Reaction equation

HRID 581713 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].[CH2:38]([N:40]([CH2:44][CH3:45])[CH2:41][CH2:42][NH2:43])[CH3:39].C(Cl)[Cl:47]>>[ClH:47].[ClH:47].[ClH:47].[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:43][CH2:42][CH2:41][N:40]([CH2:44][CH3:45])[CH2:38][CH3:39])=[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]2

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 60993N,N-DiethylethylenediamineHCID 682631,1'-CarbonyldiimidazoleHCID 15863846HCID 15863846, compound

Product 2

HCID 313Hydrochloric AcidHCID 131721300HCID 131721300, compound

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 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.

Workup

  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

Sources & evidence

ORD record
ord-3df8cc3846d94578a24cff9f42c2853b
Source dataset
uspto-grants-1999_07
Patent number
US05922703

Reaction notes

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