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Phosphate → 16-(Phenylsulfinylmethyl)pregn-1,4,9(11),16-tetraene-3,20-dione

HRID 1285315
ノート
印刷プレビュー

反応式

HRID 1285315 の反応式
[C:1]1([S:7](Cl)=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([C@:13]1(O)[C:18](=[CH2:19])[CH2:17][C@H:16]2[C@H:20]3[C:30](=[CH:31][CH2:32][C@:14]12[CH3:15])[C@:28]1([CH3:29])[C:23](=[CH:24][C:25](=[O:33])[CH:26]=[CH:27]1)[CH2:22][CH2:21]3)(=[O:12])[CH3:11].P([O-])([O-])([O-])=O>C(Cl)Cl.C(N(CC)CC)C>[C:1]1([S:7]([CH2:19][C:18]2[CH2:17][C@@H:16]3[C@:14]([CH3:15])([CH2:32][CH:31]=[C:30]4[C@H:20]3[CH2:21][CH2:22][C:23]3[C@:28]4([CH3:29])[CH:27]=[CH:26][C:25](=[O:33])[CH:24]=3)[C:13]=2[C:10](=[O:12])[CH3:11])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 1061PhosphateHCID 4190003Benzenesulfinyl chlorideHCID 1357883717beta-Hydroxy-16-methylenepregna-1,4,9(11)-triene-3,20-dione

生成物 1

HCID 5718204716-(Phenylsulfinylmethyl)pregn-1,4,9(11),16-tetraene-3,20-dione

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒2 回
HCID 8471
Triethylamine
溶媒

実験手順

Phenylsulfinyl chloride in methylene chloride (2.5N, 2.4 ml) was added to a mixture of 17α-acetyl-17β-hydroxy-16-methyleneandrost-1,4,9(11)-trien-3-one (VB, Example 17, 1 g) in methylene chloride (10 ml) and triethylamine (0.82 ml) previously cooled to -30° over a period of 2 hrs. The reaction is plunged into phosphate buffer (pH 7, 10 ml); the phases are separated; the aqueous phase is extracted with methylene chloride; the organic phases are combined and dried over sodium sulfate and concentrated under reduced presure to an isomeric mixture of the title compound. The isomers are separated by chromatography on silica gel (50 g), eluting with acetone/hexane: 5/95 to give the title compound, NMR (CDCl3) 0.89, 1.42, 2.10, 4.03, 5.5, 6.0, 6.27, 7.20 δ.

後処理

  1. temperaturepreviously cooled to -30° over a period of 2 hrs
  2. customthe phases are separated
  3. extractionthe aqueous phase is extracted with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced presure to an isomeric mixture of the title compound
  6. customThe isomers are separated by chromatography on silica gel (50 g)
  7. washeluting with acetone/hexane

出典と根拠

ORDレコード
ord-f7977debaa2e407ebe39837cb647285f
出典データセット
uspto-grants-1986_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04567001

反応ノート

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