1,4-Dioxane hydrochloride → (2R,4S)-2-Aminomethyl-4-ethyl-heptanoic Acid

Participants

Reaction Conditions

Reaction Steps

A stirred solution of (2S,5R)-2-tert-butyl-5-((S)-2-ethyl-pentyl)-3-methyl-4-oxo-tetrahydro-pyrimidine-1-carboxylic acid methyl ester (0.185 g, 0.567 mmol) in a 1:1 mixture of 6N HCl/dioxane (8 mL) was heated at 105° C. for 6 days. The reaction was cooled to room temperature and concentrated under reduced pressure. The product was dissolved in 1:1 MeOH/H2O and loaded onto an ion exchange chromatography column (Varian SCX-Prepacked 10 g, 60 mL) and eluted with 1:1 MeOH/H2O (95%)+NH4OH. The fractions containing product were collected and concentrated under reduced pressure to yield 0.06 g (57%) of product: 1H NMR (400 MHz, CD3OD) δ ppm 0.9 (m, 6 H), 1.3 (m, 5 H), 1.4 (m, 3 H) 1.7 (m, 1 H), 2.5 (m, 1 H), 2.9 (d, J=6.6 Hz, 2 H). MS: M+1 (188).

Provenance & Evidence