Methanol → Methyl 2-(3-aminoazetidin-1-yl)-4-ethyl-1,3-thiazole-5-carboxylate

A 4 N hydrochloric acid/ethyl acetate solution (1.02 mL, 4.07 mmol) was added to a solution of methyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-ethyl-1,3-thiazole-5-carboxylate obtained in Example (222a) (139 mg, 0.41 mmol) in 1,4-dioxane (4 mL) at room temperature, and the mixture was stirred at room temperature for 13 hours. Then, methanol (2 mL) was added, and the mixture was further stirred for 5.5 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 94 mg of the title compound as a pale yellow oily substance (96%).

1. stirringthe mixture was further stirred for 5.5 hours
2. concentrationThe reaction solution was concentrated
3. additionsaturated aqueous sodium bicarbonate solution was added to the resulting residue
4. extractionThereafter, the mixture was extracted with ethyl acetate
5. dry with materialthe combined organic layers were dried over anhydrous magnesium sulfate
6. filtrationfiltration
7. customthe solvent was evaporated under reduced pressure

ORD record

ord-9d68be2524e74786b8714b4143623ba0

Source dataset

uspto-grants-2013_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08536197B2