Hydrochloric Acid → 2-(1-((Tert-butoxy)carbonyl)-3-hydroxyazetidin-3-yl)acetic acid
Reaction equation
C([O:5][C:6](=[O:20])[CH2:7][C:8]1([OH:19])[CH2:11][N:10]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:9]1)(C)(C)C.Cl.[OH-].[Na+].O(C(OC(C)(C)C)=O)C(OC(C)(C)C)=O>O1CCOCC1>[C:12]([N:10]1[CH2:9][C:8]([CH2:7][C:6]([OH:20])=[O:5])([OH:19])[CH2:11]1)([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
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).
Workup
- temperatureThe reaction mixture was then cooled to 0° C.
- temperatureto warm to room temperature for 2 h
- concentrationwas then concentrated to half its total volume on the rotary evaporator
- additionIsopropanol (3 mL) and chloroform (12 mL) were then added
- temperaturethe mixture was cooled to 0° C.
- customThe organic layer was then separated
- dry with materialdried over Na2SO4
- concentrationconcentrated to dryness
Sources & evidence
- ORD record
- ord-105d5c8a1d8f40e1b122edba25c2bb5f
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08383596B2
Reaction notes
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