p-Toluenesulfonic acid → HCID 178441215, Verbindung

HRID 852789

Reaktionsgleichung

Reaktionsgleichung von HRID 852789
[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:24][C:25]([CH3:27])=[CH2:26])([CH2:15][CH2:16][O:17]C2CCCCO2)[C:12](=[O:14])[N:13]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[C@@H:1]12[CH2:7][C@@H:4]([CH2:5][CH2:6]1)[CH2:3][C@@H:2]2[NH:8][C:9]1[S:10][C:11]([CH2:15][CH2:16][OH:17])([CH2:24][C:25]([CH3:27])=[CH2:26])[C:12](=[O:14])[N:13]=1

Komponenten

4

Edukt 2

HCID 6101p-Toluenesulfonic acidHCID 178441184HCID 178441184, Verbindung

Produkt 1

HCID 178441215HCID 178441215, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The mixture of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-methylallyl)-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)thiazol-4(5H)-one (420 mg, 1.07 mmol) and p-toluenesulfonic acid (100 mg) in MeOH (5.0 mL) was stirred for 16 h at room temperature. The reaction mixture was then concentrated in vacuo, and sat'd NaH2PO4 was added. The mixture was then extracted with EtOAc, and the organic layer was washed with sat'd NH4Cl, dried over MgSO4, filtered and concentrated in vacuo. The crude residue was purified by flash chromatography (4:1; Hexane:EtOAc) to give the title compound as solid. MS (ES+): 309 (M+H)+.

Aufarbeitung

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. additionwas added
  3. extractionThe mixture was then extracted with EtOAc
  4. washthe organic layer was washed with sat'd NH4Cl
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography (4:1; Hexane:EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-70293bbc521a4b9f98430b498ad6e563
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253196B2

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