m-Chloroperbenzoic acid → HCID 178472329, Verbindung

HRID 928144Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928144
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

Komponenten

4

Edukt 2

HCID 70297m-Chloroperbenzoic acidHCID 178437588HCID 178437588, Verbindung

Produkt 1

HCID 178472329HCID 178472329, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d38a2a6b36054491a4852b09ee16963e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290490B2

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