Trifluoroacetic acid → HCID 178472361, Verbindung

HRID 928116Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 928116
[Br:1][C:2]1[S:6][C:5]([C:7]2([C@H:10]3[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]3)[CH2:9][O:8]2)=[N:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([CH:7]([C@H:10]2[CH2:15][CH2:14][C@H:13]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12][CH2:11]2)[CH2:9][OH:8])=[N:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 178472329HCID 178472329, Verbindung

Produkt 1

HCID 178472361HCID 178472361, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution in DCM (0.7 mL) of ethyl trans-4-[2-(5-bromo-1,3-thiazol-2-yl)oxiran-2-yl]cyclohexanecarboxylate (30 mg, 0.082 mmol) from Step 2 was treated with trifluoroacetic acid (0.266 mL, 1.665 mmol) and triethylsilane (0.128 mL, 1.665 mmol) and left at 45° C. 16 h. The volatiles were removed under reduced pressure and the residue was taken up in dichloromethane, washed with saturated sodium bicarbonate, brine, dried over magnesium sulfate, filtered and concentrated in vacuo to afford racemic ethyl trans-4-[1-(5-bromo-1,3-thiazol-2-yl)-2-hydroxyethyl]cyclohexanecarboxylate which was used as such without further characterization. MS ESI calc'd. for C14H20BrNO3S [M+H]+ 362, 364, found 362, 364.

Aufarbeitung

  1. waitleft at 45° C
  2. custom16 h
  3. customThe volatiles were removed under reduced pressure
  4. washwashed with saturated sodium bicarbonate, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-823ca7f188f041e3af218088e6678582
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09290490B2

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