Réaction #6861

ord-366c487f99fe4d4cb442dff8b04764dd

Équation de réaction

CO
MeOH
O=C(O)/C=C/c1cnc[nH]1
Urocanic acid
O=C(O)/C=C/c1cnc[nH]1
compound i
O=C(O)/C=C/c1cnc[nH]1
Urocanic acid
→
O=C(O)CCc1cnc[nH]1
3-(1H-Imidazol-5-yl)-propionic acid

Réactifs

CO
MeOH
O=C(O)/C=C/c1cnc[nH]1
Urocanic acid
O=C(O)/C=C/c1cnc[nH]1
compound i
O=C(O)/C=C/c1cnc[nH]1
Urocanic acid

Réactifs

[Pd]
Pd on carbon

Solvants

Cl
HCl

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    AutreThe catalyst was removed by filtration through a 3 cm pad of diatomaceous earth
  2. 2
    Concentrationthe filtrate was concentrated to a solid
  3. 3
    Autredried overnight under vacuum
  4. 4
    AutreThe crude material was used without further purification

Mode opératoire

Urocanic acid (compound i, where R2 is H)(1.38 g, 10.0 mmol) was dissolved in 5% aqueous HCl (20 ml) plus MeOH (15 ml) containing 10% Pd on carbon (100 mg) and the mixture was shaken overnight under about 30 psi H2. The catalyst was removed by filtration through a 3 cm pad of diatomaceous earth and the filtrate was concentrated to a solid and dried overnight under vacuum. The crude material was used without further purification. Mass spec. 141.4 MH+

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US07084135B1uspto-grants-2006_08