Methanol → Ethyl 2-(3-aminoazetidin-1-yl)-1,3-benzothiazole-7-carboxylate

A 4 N hydrochloric acid/ethyl acetate solution (2.66 mL, 10.7 mmol) and methanol (5 mL) were added to a solution of ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-7-carboxylate obtained in Example (224a) (402 mg, 1.07 mmol) in 1,4-dioxane (11 mL) at room temperature, followed by stirring for 17 hours. Then, THF (5 mL) was added, and the mixture was further stirred for 31 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 281 mg of the title compound as a pale yellow solid (95%).

1. stirringthe mixture was further stirred for 31 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-aae51b9997fe4daf9d06c6bae8b4efaa

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08927588B2