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Edetate Sodium → 17alpha-Hydroxy-20,21-epoxy-20-phenoxypregna-4,9(11)-diene-3-one

HRID 65343
Notes
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Reaction equation

HRID 65343 reaction equation
[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3]([O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[CH2:4].[OH-].[K+].[OH:33]OS([O-])=O.[K+].OS([O-])(=O)=O.[K+].C(N(CC([O-])=O)CC([O-])=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+].[Na+].[Na+]>P([O-])([O-])([O-])=O.[K+].[K+].[K+].O.CC(C)=O.CCOCC.C(Cl)Cl>[OH:1][C@:2]1([C@:28]2([CH3:29])[C@H:14]([C@H:15]3[C:25](=[CH:26][CH2:27]2)[C@:23]2([CH3:24])[C:18](=[CH:19][C:20](=[O:30])[CH2:21][CH2:22]2)[CH2:17][CH2:16]3)[CH2:13][CH2:12]1)[C:3]1([O:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[O:33][CH2:4]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

11

Reactant 5

HCID 6144Edetate SodiumHCID 14797Potassium Hydroxide2×HCID 516920Potassium bisulfateHCID 1382382517alpha-Hydroxy-20-phenoxypregna-4,9(11),20-trien-3-oneHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 56624370
17alpha-Hydroxy-20,21-epoxy-20-phenoxypregna-4,9(11)-diene-3-one

Reagents, catalysts & solvents 5

HCID 180AcetoneSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 62657Potassium Phosphate, TribasicSolvent

Procedure

17α-hydroxy-20-phenoxypregna-4,9(11),20-trien-3-one (4.04 grams, 10 mmoles) is slurried in pH 8 potassium phosphate buffer (50 ml, 0.02M PO4 57 ), 40 ml methylene chloride, 0.222 grams (1 mmole), of Ansul ether 181 (C10H22O5) and 20 ml acetone and the two phase mixture heated to 25° C. and adjusted to pH 8.5 with 30% potassium hydroxide. 18.4 grams, 30 mmoles of OXONE® (2KHSO5.KHSO4.K2SO4) is dissolved in 90 ml of water and 10 ml of a 5% by weight solution of Na4EDTA and the resulting solution added dropwise at 25° C. with vigorous agitation while maintaining the pH at 8.0-8.5 with 30% potassium hydroxide. When the reaction is complete the phases are separated hot and the aqueous phase extracted twice with 50 ml of methylene chloride. The combined organics are washed twice with 100 ml of aqueous 5% sodium hydroxide and clarified thru a solka flok filter and concentrated on a rotary evaporator to yield 17α-hydroxy-20,21-epoxy-20-phenoxypregna-4,9(11)-diene-3-one.

Workup

  1. customare separated hot
  2. extractionthe aqueous phase extracted twice with 50 ml of methylene chloride
  3. washThe combined organics are washed twice with 100 ml of aqueous 5% sodium hydroxide
  4. filtrationfilter
  5. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-f6162b161d614a6b80ca3cfa04173ed9
Source dataset
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04613463

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes