Ethyl Acetate → HCID 19593628, compound

Participants

Reaction Steps

A solution of ethyl 2-amino-4-thiazolglyoxylate (10 g, 50 mmol) in anhydrous THF (150 mL) was added dropwise to a suspension of lithium aluminum hydride (1.9 g) in anhydrous THF (200 mL), and the mixture stirred under nitrogen at RT for 1 h. Excess ethyl acetate was then added to destroy residual reductant, after which an excess of Glauber's Salt was added and the resultant suspension stirred at RT for 40 min. The slurry was then filtered, and the filtrate evaporated in vacuo, and then dissolved in methanol and adsorbed onto silica gel. This mixture was then applied to a flash silica column, and the product eluted using 10% methanol in dichloromethane. Homogenous fractions were combined and evaporated under vacuum to give (±)-2-amino-4-(1,2-dihydroxyethyl)-1,3-thiazole product as a pale orange colored solid, (2.6 g, 32.5%) with the following structure: ##STR42##

Provenance & Evidence