Water → (2beta,3alpha,5alpha)-21-(Acetylthio)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

HRID 233495Notes

Reaction equation

HRID 233495 reaction equation
[C:1]([O-:4])(=[S:3])[CH3:2].[K+].Cl[CH2:7][C:8](=[O:38])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:37])[C@@H:19]([N:29]4[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]4)[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1.O>C(O)C>[C:1]([S:3][CH2:7][C:8](=[O:38])[C@@H:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@H:23]([C:24](=[O:28])[CH2:25]2)[C@:21]2([CH3:22])[C@H:16]([CH2:17][C@H:18]([OH:37])[C@@H:19]([N:29]4[CH2:34][CH2:33][O:32][C:31]([CH3:36])([CH3:35])[CH2:30]4)[CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)(=[O:4])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10672358(2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dioneHCID 23670855Potassium ethanethioate

Product 1

HCID 10577865(2beta,3alpha,5alpha)-21-(Acetylthio)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dioneYield 60.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Potassium thioacetate (1.32 g) was added to a solution of the 21-chloro-compound of Example 2 (2.22 g) in ethanol (11.1 ml). The mixture was heated under reflux in an atmosphere of nitrogen for 40 min and then poured into water (100 ml). The precipitated solid was filtered off, washed with water and dissolved in dichloromethane. After drying the solution over sodium sulfate the solvent was removed under reduced pressure and the residue was chromatographed on silica gel. The purified product was crystallised from methanol to give (2β,3α,5α)-21-(acetylthio)-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (1.46 g). m.p. 181°-182° C.; [α]D +131.9° (c 0.88).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux in an atmosphere of nitrogen for 40 min
  3. filtrationThe precipitated solid was filtered off
  4. washwashed with water
  5. dissolutiondissolved in dichloromethane
  6. dry with materialAfter drying the solution over sodium sulfate the solvent
  7. customwas removed under reduced pressure
  8. customthe residue was chromatographed on silica gel
  9. customThe purified product was crystallised from methanol

Sources & evidence

ORD record
ord-0ca7d4a6a93b480ba431d434203e08f8
Source dataset
uspto-grants-1997_01
Patent number
US05593983

Reaction notes

Loading…