Borate → 4-Acetamino-6,7-epoxy-androsta-1,4-diene-3,17-dione

HRID 1440974ノート

反応式

HRID 1440974 の反応式
[NH:1]([C:5]1[C:22](=[O:23])[CH:21]=[CH:20][C@@:19]2([CH3:24])[C:6]=1[CH:7]=[CH:8][C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C:13]2=[O:25])[C:2]([CH3:4])=[O:3].B([O-])([O-])[O-:27].ClC1C=CC=C(C(OO)=O)C=1.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[NH:1]([C:5]1[C:22](=[O:23])[CH:21]=[CH:20][C@@:19]2([CH3:24])[C:6]=1[CH:7]1[O:27][CH:8]1[C@@H:9]1[C@@H:18]2[CH2:17][CH2:16][C@@:14]2([CH3:15])[C@H:10]1[CH2:11][CH2:12][C:13]2=[O:25])[C:2]([CH3:4])=[O:3]

参加物

6

反応物 4

HCID 26574BorateHCID 70297m-Chloroperbenzoic acidHCID 656671Sodium PyrosulfiteHCID 228594964-Acetamino-androsta-1,4,6-triene-3,17-dione

生成物 1

HCID 538134384-Acetamino-6,7-epoxy-androsta-1,4-diene-3,17-dione収率 50%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of 4-acetamino-androsta-1,4,6-triene-3,17-dione (3.384 g, 10 mmol) in CH2Cl2 (100 ml) was added borate buffer of pH 8 (50 ml) and then gradually 50% m-chloroperbenzoic acid (6.9 g, 20 mmol) under cooling. The mixture was stirred for 6 h at room temperature until total conversion (TLC monitoring). The mixture was then stirred with 20% sodium metabisulfite solution for 1 h at room temperature. Finally the organic phase was separated, dried and evaporated under vacuum. The residue was submitted to flash chromatography on silica gel with EtOAc thus giving pure title compound in 50% yield (1.772 g).

後処理

  1. customFinally the organic phase was separated
  2. customdried
  3. customevaporated under vacuum

出典と根拠

ORDレコード
ord-1061e77345b34ada95bb04e06cf2d3ca
出典データセット
uspto-grants-1996_03
特許番号
US05502044

反応ノート

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