m-Chloroperbenzoic acid → HCID 178472329, 화합물

HRID 928144노트

반응식

HRID 928144 반응식
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

참가 물질

4

반응물 2

HCID 70297m-Chloroperbenzoic acidHCID 178437588HCID 178437588, 화합물

생성물 1

HCID 178472329HCID 178472329, 화합물

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d38a2a6b36054491a4852b09ee16963e
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290490B2

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