Reaktion #74401

ord-4d310588096c413591ea91d49146f949

Reaktionsgleichung

O=C1N=C(N[C@H]2C[C@@H]3CC[C@H]2C3)SC1CCO
2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-hydroxyethyl)thiazol-4(5H)-one
C1=COCCC1
3,4-dihydro-2H-pyran
→
O=C1N=C(N[C@H]2C[C@@H]3CC[C@H]2C3)SC1CCOC1CCCCO1
title compound
O=C1N=C(N[C@H]2C[C@@H]3CC[C@H]2C3)SC1CCOC1CCCCO1
2-((1S,2S,4R)-Bicyclo[2.2.1]heptan-2-ylamino)-5-(2-(tetrahydro-2H-pyran-2-yloxy)ethyl)thiazol-4(5H)-one

Edukte

—
acid
O=C1N=C(N[C@H]2C[C@@H]3CC[C@H]2C3)SC1CCO
2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-hydroxyethyl)thiazol-4(5H)-one
C1=COCCC1
3,4-dihydro-2H-pyran

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Waschenwashed with sat'd NaH2PO4
  2. 2
    Trocknendried over MgSO4
  3. 3
    FiltrationAfter being filtered
  4. 4
    Einengenconcentrated in vacuo
  5. 5
    Sonstigethe crude residue was purified by flash chromatography (3:2; Hexane:EtOAc)

Vorschrift

The mixture of 2-((1S,2S,4R)-bicyclo[2.2.1]heptan-2-ylamino)-5-(2-hydroxyethyl)thiazol-4(5H)-one (3.2 g, 12.6 mmol) and p-toulenesulfonic acid (500 mg) in 3,4-dihydro-2H-pyran (10 mL) was stirred for 2 h at room temperature. The resulting mixture was diluted with CH2Cl2 (100 mL), then washed with sat'd NaH2PO4, and dried over MgSO4. After being filtered and concentrated in vacuo, the crude residue was purified by flash chromatography (3:2; Hexane:EtOAc) to give the title compound as an oil. MS (ES+): 339 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08541592B2uspto-grants-2013_09