Triethylamine → 17-Acetylthiomethyl-1alpha,3beta-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene

HRID 1792168ノート

反応式

HRID 1792168 の反応式
[Si:1]([O:8][C@@H:9]1[C@@:26]2([CH3:27])[C:13](=[CH:14][CH:15]=[C:16]3[C@@H:25]2[CH2:24][CH2:23][C@@:21]2([CH3:22])[C@H:17]3[CH2:18][CH:19]=[C:20]2[CH2:28]O)[CH2:12][C@@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C(N(CC)CC)C.CS(Cl)(=O)=O.[C:50]([O-:53])(=[S:52])[CH3:51].[K+]>O1CCCC1.CS(C)=O.CCCCCC>[C:50]([S:52][CH2:28][C:20]1[C@:21]2([CH2:23][CH2:24][C@H:25]3[C:16](=[CH:15][CH:14]=[C:13]4[C@:26]3([CH3:27])[C@@H:9]([O:8][Si:1]([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3])[CH2:10][C@H:11]([O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:32])[CH3:33])[CH2:12]4)[C@@H:17]2[CH2:18][CH:19]=1)[CH3:22])(=[O:53])[CH3:51]

参加物

8

反応物 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 23670855Potassium ethanethioateHCID 673014381alpha,3beta-Bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene

生成物 1

HCID 8658997017-Acetylthiomethyl-1alpha,3beta-bis(tert-butyldimethylsilyloxy)androsta-5,7,16-triene収率 88.3%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

実験手順

To a solution of 1α,3β-bis(tert-butyldimethylsilyloxy)-17-(hydroxymethyl)androsta-5,7,16-triene (4.00 g, 7.34 mmol) in tetrahydrofuran (70 ml), was added triethylamine (4.10 ml, 29.4 mmol), followed by the dropwise addition of methanesulfonyl chloride (1.70 ml, 22.0 mmol) at −10° C. and stirring for 20 min. The reaction mixture was warmed to room temperature and a solution of potassium thioacetate (3.73 g, 29.4 mmol) in dimethylsulfoxide (70 ml) was added. After stirring for 30 min., the mixture was diluted with hexane, washed with water, the organic layer was dried over anhydrous magnesium sulfate and evaporated for removing the solvent. The thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1) to give the titled compound (3.91 g, 88%) as a colorless oil.

後処理

  1. stirringAfter stirring for 30 min.
  2. washwashed with water
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. customevaporated
  5. customfor removing the solvent
  6. customThe thus obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=15:1)

出典と根拠

ORDレコード
ord-399cca0fbbf6451b89afcb477ad98cfd
出典データセット
uspto-grants-2006_07
特許番号
US07074777B2

反応ノート

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