Réaction #72155

Équation de réaction

hydrochloric acid ethyl acetate

ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-methyl-1,3-thiazole-5-carboxylate

Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-methyl-1,3-thiazole-5-carboxylate

hydrochloric acid ethyl acetate

→

title compound

Rendement 79.6%

Ethyl 2-(3-aminoazetidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

Rendement 79.6%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

1. 1
   workup.STIRRINGthe mixture was further stirred for 45 hours
2. 2
   ConcentrationThe reaction solution was concentrated
3. 3
   workup.ADDITIONsaturated aqueous sodium bicarbonate solution was added to the resulting residue
4. 4
   ExtractionThereafter, the mixture was extracted with ethyl acetate
5. 5
   Séchagethe combined organic layers were dried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltration
7. 7
   Autrethe solvent was evaporated under reduced pressure

Mode opératoire

A 4 N hydrochloric acid/ethyl acetate solution (0.96 mL, 3.82 mmol) was added to a solution of ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (218a) (261 mg, 0.76 mmol) in 1,4-dioxane (8 mL) at 0° C., and the mixture was stirred at room temperature for 7.5 hours. Then, a 4 N hydrochloric acid/ethyl acetate solution (0.96 mL, 3.82 mmol) was added, and the mixture was further stirred for 45 hours. The reaction solution was concentrated, and saturated aqueous sodium bicarbonate solution was added to the resulting residue. Thereafter, the mixture was extracted with ethyl acetate, and the combined organic layers were dried over anhydrous magnesium sulfate. Following filtration, the solvent was evaporated under reduced pressure to obtain 146 mg of the title compound as a pale yellow oily substance (79%).

Source