Reaktion #74427

ord-117633cd925b4ad782388613026d325d

Reaktionsgleichung

CC(C)C1(C)SC(N[C@H]2CCCC[C@@H]2OCc2ccccc2)=NC1=O
2-((1S,2S)-2-(benzyloxy)cyclohexylamino)-5-isopropyl-5-methylthiazol-4(5H)-one
C[Si](C)(C)I
iodotrimethylsilane
→
CC(C)C1(C)SC(N[C@H]2CCCC[C@@H]2O)=NC1=O
2-((1S,2S)-2-hydroxycyclohexylamino)-5-isopropyl-5-methylthiazol-4(5H)-one

Edukte

CC(C)C1(C)SC(N[C@H]2CCCC[C@@H]2OCc2ccccc2)=NC1=O
2-((1S,2S)-2-(benzyloxy)cyclohexylamino)-5-isopropyl-5-methylthiazol-4(5H)-one
C[Si](C)(C)I
iodotrimethylsilane

Reagenzien

Keine

Lösungsmittel

ClCCl
DCM

Reaktionsbedingungen

Temperatur
65°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe vial was sealed
  2. 2
    EinengenThe reaction was concentrated
  3. 3
    Sonstigepurified by column chromatography (2% to 7% MeOH/DCM)

Vorschrift

A 5 mL vial was charged with 2-((1S,2S)-2-(benzyloxy)cyclohexylamino)-5-isopropyl-5-methylthiazol-4(5H)-one (0.100 g, 0.28 mmol) and 1 mL of DCM. To this was added iodotrimethylsilane (0.22 g, 1.1 mmol). The vial was sealed and heated at 65° C. for 36 h. The reaction was concentrated and purified by column chromatography (2% to 7% MeOH/DCM) to give 2-((1S,2S)-2-hydroxycyclohexylamino)-5-isopropyl-5-methylthiazol-4(5H)-one as a yellow solid

Quelle

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