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

HRID 65343

反応式

HRID 65343 の反応式
[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

参加物

11

反応物 5

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

生成物 1

HCID 5662437017alpha-Hydroxy-20,21-epoxy-20-phenoxypregna-4,9(11)-diene-3-one

試薬・触媒・溶媒 5

HCID 180Acetone溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6344Dichloromethane溶媒HCID 62657Potassium Phosphate, Tribasic溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f6162b161d614a6b80ca3cfa04173ed9
出典データセット
uspto-grants-1986_09
特許番号
US04613463

関連ノート

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