Ethyl Acetate → HCID 19593628, compound

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-(1,2-dihydroxyethyl)-1,3-thiazole product as a pale orange colored solid, (2.6 g, 32.5%) with the following structure: ##STR43##

1. customto destroy residual reductant
2. additionafter which an excess of Glauber's Salt was added
3. stirringthe resultant suspension stirred at RT for 40 min
4. filtrationThe slurry was then filtered
5. customthe filtrate evaporated in vacuo
6. dissolutiondissolved in methanol
7. washthe product eluted
8. customevaporated under vacuum

ORD record

ord-7df395dabfa1469caafb94db1c8ee21b

Source dataset

uspto-grants-1999_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05919965