Diisopropylethylamine → 3-(2-Amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid

Beteiligte Stoffe

Reaktionsschritte

5-thiocyanato-thiazol-2-ylamine (15.7 g) was dissolved in degassed methanol and sodium borohydride (4.5 g) in MeOH was added in one portion. The reaction was stirred for 30 min and 3-bromo-2,2-dimethyl-propionic acid (27 g) (prepared in the same manner as described by Greene at al, J Am Chem Soc 1955, 77, 3016) and diisopropylethylamine (17 mL) was added and the reaction stirred overnight at room temperature. The reaction was diluted with water, partially concentrated in vacuo and 5% citric acid was added until pH 4. The brown precipitate was filtered, washed with water and acetonitrile, and dried over night at room temperature to give 3-(2-amino-thiazol-5-ylsulfanyl)-2,2-dimethyl-propionic acid as light brown crystals.

Herkunft & Nachweise