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

HRID 233521
Notes
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Reaction equation

HRID 233521 reaction equation
Cl[CH2:2][C:3](=[O:33])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:32])[C@@H:14]([N:24]4[CH2:29][CH2:28][O:27][C:26]([CH3:31])([CH3:30])[CH2:25]4)[CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[N-:34]=[N+:35]=[N-:36].[Na+].CN(C)C=O>CO.O>[N:34]([CH2:2][C:3](=[O:33])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C@H:13]([OH:32])[C@@H:14]([N:24]4[CH2:29][CH2:28][O:27][C:26]([CH3:31])([CH3:30])[CH2:25]4)[CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1)=[N+:35]=[N-:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 10672358(2beta,3alpha,5alpha)-21-Chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione

Product 1

HCID 10624805(2beta,3alpha,5alpha)-21-Azido-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dioneYield 34.7%

Reagents, catalysts & solvents 2

HCID 887
Methanol
Solvent
HCID 962WaterSolvent2×

Procedure

A stirred mixture of (2β,3α,5α)-21-chloro-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (500 mg), sodium azide (140 mg), N,N-dimethylformamide (1.25 ml) in methanol (10 ml) and water (0.25 ml) was heated under reflux for 2 h, then cooled and poured into water (50 ml). The resulting precipitate was filtered off and dissolved in dichloromethane. After washing the solution with water and drying over sodium sulfate, the solvent was removed under reduced pressure and the residue (422 mg) was chromatographed on silica gel. The purified product was crystallised from dichloromethane-methanol to give (2β,3α,5α)-21-azido-3-hydroxy-2-(2,2-dimethyl-4-morpholinyl)pregnane-11,20-dione (176 mg). δ (CDCl3) 0.62 (s,3H), 1.06 (s,3H), 1.22 (s,3H), 1.24 (s,3H) and 3.85 (s,2H).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 h
  3. temperaturecooled
  4. filtrationThe resulting precipitate was filtered off
  5. dissolutiondissolved in dichloromethane
  6. washAfter washing the solution with water
  7. dry with materialdrying over sodium sulfate
  8. customthe solvent was removed under reduced pressure
  9. customthe residue (422 mg) was chromatographed on silica gel
  10. customThe purified product was crystallised from dichloromethane-methanol

Sources & evidence

ORD record
ord-2d6eebd6333243ff822ed04f501c97fc
Source dataset
uspto-grants-1997_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05593983

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes