2-Oxo-4-phenylbutyric acid → HCID 13105154, compound

Participants

Reaction Steps

A mixture of 4-phenyl-2-oxobutyric acid (1.49 g) and L-alanyl-L-proline (0.31 g) in water are adjusted to pH 7.5 with caustic and treated with sodium cyanoborohydride (0.32 g) overnight. The product is absorbed on strong acid ion exchange resin and eluted with 2% pyridine in water to give 0.36 g of crude diastereomeric product, N-(1-carboxy-3-phenylpropyl)-L-alanyl-L-proline. A portion is purified by gel filtration (LH-20) for spectrographic analysis. The nmr spectrum in DMSO shows aromatic hydrogen at 7.20, a broad singlet at 4.30, broad multiplets at 3.0 to 3.9, 2.67 and 1.94, and a doublet at 1.23 and 1.15. The mass spectrum shows a molecular ion at 492 m/e for the ditrimethylsilylated species.

Provenance & Evidence