Abstract
The title compound, C22H25NO5, was prepared by CAN [cerium(IV) ammonium nitrate] oxidation of the corresponding β-lactam. The dihedral angle between the benzene rings is 13.3 (4)° and the C-N-C(=O)-C torsion angle is 176.1 (6)°. In the crystal, amide-C(4) N-H⋯O and reinforcing C-H⋯O hydrogen bonds link the mol-ecules into infinite [010] chains. Further C-H⋯O hydrogen bonds cross-link the chains in the c-axis direction.
Highlights
The title compound, C22H25NO5, was prepared by CAN [cerium(IV) ammonium nitrate] oxidation of the corresponding -lactam
Cerium(IV) ammonium nitrate (CAN) is a powerful reagent in organic synthesis, which promotes a wide range of reactions that go well beyond its usual role as an oxidant
Chemoselective mono-debenzylation of benzyl tertiary amines occurs in the presence of N-benzyl amides, O-benzyl ethers and esters (Bull et al, 2000); interestingly this reaction can be applied to mono-debenzylation of
Summary
Cerium(IV) ammonium nitrate (CAN) is a powerful reagent in organic synthesis, which promotes a wide range of reactions that go well beyond its usual role as an oxidant -amino esters as a way to obtain -lactams (Davies & Ichihara, 1998) or piperidone (Garrido et al, 2011), providing as well a new oxidative methodology as catch linker for reaction monitoring and optimization on solid phase support (Davies et al, 2008). Derivatives with application to the synthesis of non-peptidic neurokinin NK1 receptor antagonist (+)-L-733,060 (Garrido et al, 2010). Within this context of the synthesis of biologically active compounds, we are interested in the synthesis of. For the CAN oxidation reaction of a related trialkyl amine derivative providing monodeprotection, see Garrido et al. Acta Cryst. Symmetry codes: (i) x; y þ 1; z; (ii) x; y þ 12; z þ 52
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