The Synthesis of DL-Lysine from Dihydropyran

The α-Amino-ι-Hydroxamino Acids*

“…Exactly 6.4 mmoles of compound IVa or IVb (1.4 g IVa, preceding synthesis; 1.5 g IVb, Gaudry, 1948, andRogers et al, 1949), 0.75 g urea, and 10 ml of dimethyl formamide were placed in a 50-ml round-bottomed flask suspended in a constant-temperature bath at 30°. A magnetic stirring bar was dropped in, 0.75 g (10.9 mmoles) of NaNOj was added, the flask was closed with a CaClj tube, and the magnetic stirrer was adjusted to gentle agitation.…”

Food For Tomorrow

“…But most efforts that have been made to obtain this diamino acid failed because of low yield or the unsuitability of the intermediary products (36). However, recently Rogers and coworkers developed in the laboratories of Du Pont Co. a method by which dllysine is obtained from the easily available dihydropvran and hydroxvbutylhydantoin and which appears to be well suited for production on an industrial scale (34). There still remained the difficulty that the product so obtained is a racemic mixture of l-and D-forms, as lysine belongs to those amino acids which can be assimilated only in their L-form.…”

α-Oximinoketones. V. The Synthesis of 5-Cyano-2-oximinovaleric Acid and DL-Lysine from 2,6-Dioximinocyclohexanone1

“…Perhaps the largest number of published syntheses have proceeded from e-caprolactam (most commonly prepared by Beckmann rearrangement of cyclohexanone oxime).3 456Other favorite starting materials have been malonic ester4-6 or its derivative, acetamidomalonic ester.7•8 Several elegant syntheses have been based on oxygen-containing heterocyclic materials such as acrolein dimer (3,4-dihydro-2H-pyran-2-carboxaldehyde)9 10**or furfural. [10][11][12] (1) A preliminary account of this and the next two papers in this series was published in Chem. & Ind.…”