Citric Acid → (2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-11-one-17-carbonitrile 2-hydroxy-1,2,3-propanetricarboxylate

HRID 233528Notes

Reaction equation

HRID 233528 reaction equation
[OH:1][C@@H:2]1[C@@H:19]([N:20]2[CH2:25][CH2:24][O:23][C:22]([CH3:27])([CH3:26])[CH2:21]2)[CH2:18][C@@:17]2([CH3:28])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:29])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:30]#[N:31])[CH2:3]1.[C:32]([OH:44])(=[O:43])[CH2:33][C:34]([CH2:39][C:40]([OH:42])=[O:41])([C:36]([OH:38])=[O:37])[OH:35]>C(O)C>[OH:1][C@@H:2]1[C@@H:19]([N:20]2[CH2:25][CH2:24][O:23][C:22]([CH3:26])([CH3:27])[CH2:21]2)[CH2:18][C@@:17]2([CH3:28])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:16]2[C:15](=[O:29])[CH2:14][C@@:12]2([CH3:13])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:30]#[N:31])[CH2:3]1.[OH:35][C:34]([C:36]([O-:38])=[O:37])([CH2:39][C:40]([O-:42])=[O:41])[CH2:33][C:32]([O-:44])=[O:43]

Participants

4

Reactant 2

HCID 311Citric AcidHCID 22868795(2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstan-11-one-17-carbonitrile

Product 1

HCID 131719790(2beta,3alpha,5alpha,17beta)-3-Hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-11-one-17-carbonitrile 2-hydroxy-1,2,3-propanetricarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-11-one-17-carbonitrile (500 mg) and citric acid (224 mg) in ethanol (5 ml) was stirred for 5 min. Removal of the solvent under reduced pressure and crystallisation from dichloromethane-diethyl ether afforded (2β,3α,5α,17β)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)androstane-11-one-17-carbonitrile 2-hydroxy-1,2,3-propanetricarboxylate (1:1) salt (427 mg). [α]D +80.8° (c 0.5).

Workup

  1. customRemoval of the solvent
  2. customunder reduced pressure and crystallisation from dichloromethane-diethyl ether

Sources & evidence

ORD record
ord-e61053942876446c820e0a40b7351274
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

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