Dicyclohexylcarbodiimide → HCID 22916736, compound

Participants

Reaction Steps

60 ml of methylene chloride was added to 3.854 g of N-tert-butoxycarbonylglycine and 2.97 g of 1-hydroxybenzotriazole. To this mixture was further added 4.54 g of dicyclohexylcarbodiimide with stirring and ice-cooling. The mixture was stirred for 2 hours with ice-cooling. To this was added 2.28 g of 2-aminomethylthiazole, and the resulting mixture was stirred for an additional 16 hours. The crystals precipitated were removed by filtration. The filtrate was washed with a 5% aqueous solution of sodium hydrogencarbonate, and dried over anhydrous magnesium sulfate. The methylene chloride was evaporated under reduced pressure. The residue was purified by flash column chromatography using silica gel, eluting with ethyl acetate to give 5.29 g (yield 97%) of 2-[(N-tert-butoxycarbonylglycyl)amino]methylthiazole.

Provenance & Evidence