Exploring solid-phase approaches for the preparation of new beta-lactams from amino acids.
Two solid-phase approaches, involving the base-assisted intramolecular alkylation of N-chloroacetyl-Phe derivatives anchored to appropriate solid supports, were investigated for the preparation of novel beta-lactams. When a BAL-type strategy was used, the resin-bound azetidinones were easily formed, as established by MAS-NMR, but final compounds could not be removed from the resin, unless a suitable two linkers system was used. In the second approach, in which the Phe residue is anchored to a Wang-type resin through the carboxylate group, the corresponding 1,4,4-trisubstituted 2-azetidinone was obtained in moderate to good yield and high purity.
Gerona-Navarro
Guillermo
G
Instituto de Química Médica (CSIC), Madrid, Spain.
Royo
Miriam
M
García-López
Ma Teresa
MT
Albericio
Fernando
F
González-Muñiz
Rosario
R
D000596:Amino Acids / Q000737:chemistry*; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis; D020650:Combinatorial Chemistry Techniques; D047090:beta-Lactams / Q000138:chemical synthesis*
D000596:Amino Acids; D000900:Anti-Bacterial Agents; D047090:beta-Lactams