m-Chloroperbenzoic acid → HCID 178472329、化合物

HRID 928144ノート

反応式

HRID 928144 の反応式
C1C=C(Cl)C=C(C(OO)=[O:9])C=1.[Br:12][C:13]1[S:17][C:16]([C:18]([C@H:20]2[CH2:25][CH2:24][C@H:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]2)=[CH2:19])=[N:15][CH:14]=1>C(Cl)Cl>[Br:12][C:13]1[S:17][C:16]([C:18]2([C@H:20]3[CH2:25][CH2:24][C@H:23]([C:26]([O:28][CH2:29][CH3:30])=[O:27])[CH2:22][CH2:21]3)[CH2:19][O:9]2)=[N:15][CH:14]=1

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acidHCID 178437588HCID 178437588、化合物

生成物 1

HCID 178472329HCID 178472329、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

mCPBA (130 mg, 0.582 mmol) was added was added to a solution of ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)ethenyl]cyclohexanecarboxylate (182 mg, 0.529 mmol) in DCM (3 ml) at 0° C. The mixture was then allowed to stir at room temperature for 17 h, diluted with dichlormethane and washed with sodium hydroxide (2M in H2O). The aqueous layer was extracted with DCM and the combined organic layers were washed with brine, dried, concentrated in vacuo. The residue was purified on silica gel (0-15% EtOAc in hexane) to afford ethyl trans-4-[2-(5-bromo-1,3-thiazol-2-yl)oxiran-2-yl]cyclohexanecarboxylate. MS ESI calc'd. for C14H18BrNO3S [M+H]+ 360. found 360.

後処理

  1. washwashed with sodium hydroxide (2M in H2O)
  2. extractionThe aqueous layer was extracted with DCM
  3. washthe combined organic layers were washed with brine
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified on silica gel (0-15% EtOAc in hexane)

出典と根拠

ORDレコード
ord-d38a2a6b36054491a4852b09ee16963e
出典データセット
uspto-grants-2016_03
特許番号
US09290490B2

反応ノート

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