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

HRID 1440974노트

반응식

HRID 1440974 반응식
[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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-1061e77345b34ada95bb04e06cf2d3ca
출처 데이터셋
uspto-grants-1996_03
특허 번호
US05502044

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