Dichloromethane → Hydrochloric Acid

HRID 581712Notes

Reaction equation

HRID 581712 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]([CH2:45][CH3:46])[CH2:41][CH2:42][CH2:43][NH2:44])[CH3:39].C(Cl)[Cl:48]>>[ClH:48].[ClH:48].[ClH:48].[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:44][CH2:43][CH2:42][CH2:41][N:40]([CH2:45][CH3:46])[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 61011N,N-Diethyl-1,3-propanediamineHCID 682631,1'-CarbonyldiimidazoleHCID 15863846HCID 15863846, compound

Product 2

HCID 313Hydrochloric AcidHCID 131721299HCID 131721299, 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 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.

Workup

  1. stirringto stir at ambient temperature
  2. concentrationis then 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 1.68 g of crude sticky solid
  7. customThe solid is purified via flash chromatography twice
  8. customto yield the free base

Sources & evidence

ORD record
ord-74da95c4d50a4acc9c475fb27e75d26e
Source dataset
uspto-grants-1999_07
Patent number
US05922703

Reaction notes

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