Reaction #1095849

ord-007396ff74da472dba05514217e4cb3d

Reaction equation

O=C(O)/C=C/c1cnc[nH]1
Urocanic acid
O=C(O)/C=C/c1cnc[nH]1
urocanic acid
→
O=C(O)CCc1c[nH]cn1
3-(1H-Imidazol-4-yl)propionic acid

Reactants

O=C(O)/C=C/c1cnc[nH]1
Urocanic acid
O=C(O)/C=C/c1cnc[nH]1
urocanic acid

Reagents

[Pd]
Pd/C

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Filtrationfiltered
  2. 2
    Concentrationthe filtrate was concentrated under a reduced pressure
  3. 3
    Otherto give the objective product

Procedure

Urocanic acid (3-(1H-imidazol-4-yl)-acrylic acid) (138 mg, 1 mmol) was placed in a round-bottom flask and dist MeOH was added thereto until urocanic acid was completely dissolved. To this solution, 10% Pd/C (30 mg) was added, replaced with H2 and stirred. After five hours, the loss of raw materials was confirmed, filtered, and the filtrate was concentrated under a reduced pressure to give the objective product.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07973027B2uspto-grants-2011_07