Hydrochloric Acid → 8-Guanidino-3-hydroxyoctanamide hydrochloride

Participants

Reaction Steps

To a solution of 670 mg of 8-amino-3-hydroxyoctanamide hydrochloride in 8 ml of 1N aqueous sodium hydroxide solution, was added 668 mg (2.4 mmoles) of S-methylisothiourea hemisulfate. The mixture was stirred overnight at room temperature. The reaction mixture was adjusted to pH 6 with 1N hydrochloric acid, evaporated to dryness and dissolved in 5 ml of 1M saline. The solution was passed through a column of 160 ml of Diaion® HP-20 (Mitsubishi Chemical Co.) and the column was eluted successively with 400 ml of 1M saline, 400 ml of 0.8M saline and 800 ml of 0.6M saline (15 g fraction size). Fractions No. 41 to No. 87 were combined, evaporated to dryness and extracted three times with 10 ml of methanol. The methanol layer was passed through a column of 300 ml of Sephadex® LH-20 and eluted with methanol to effect desalting (7 ml fraction size). Fractions No. 25 to 35 were combined and evaporated to dryness to obtain 687 mg (85% yield) of 8-guanidino-3-hydroxyoctanamide hydrochloride.

Provenance & Evidence