Hydrochloric Acid → 2-(1-((Tert-butoxy)carbonyl)-3-hydroxyazetidin-3-yl)acetic acid

Temperature

70 °C

To a stirring solution of tert-butyl-2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetate (0.86 g, 2.99 mmol) in dioxane (18 mL) was added 3M HCl (5 mL), and the mixture was heated at 70° C. for 1 h. The reaction mixture was then cooled to 0° C. and it was basified with 2 M NaOH (8 mL), followed by addition of BOC2O (1.0 g, 4.6 mmol). The reaction mixture was allowed to warm to room temperature for 2 h, and was then concentrated to half its total volume on the rotary evaporator. Isopropanol (3 mL) and chloroform (12 mL) were then added and the mixture was cooled to 0° C. and slowly acidified to pH 3 with 1M HCl. The organic layer was then separated, dried over Na2SO4, and concentrated to dryness to yield 2-(N-Boc-3-hydroxy-azetidin-3-yl)-acetic acid (0.65 g, 2.81 mmol, 94.0% yield).

1. temperatureThe reaction mixture was then cooled to 0° C.
2. temperatureto warm to room temperature for 2 h
3. concentrationwas then concentrated to half its total volume on the rotary evaporator
4. additionIsopropanol (3 mL) and chloroform (12 mL) were then added
5. temperaturethe mixture was cooled to 0° C.
6. customThe organic layer was then separated
7. dry with materialdried over Na2SO4
8. concentrationconcentrated to dryness

ORD record

ord-428f4b67ca0f45fe801c38a684ec6dd5

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09266919B2