Reaktionsgleichung
[C:1]([C:5]1[CH:23]=[CH:22][CH:21]=[CH:20][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:19])[CH2:13][C:14]([O:16]CC)=[O:15])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C(O)C>[C:1]([C:5]1[CH:23]=[CH:22][CH:21]=[CH:20][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:12](=[O:19])[CH2:13][C:14]([OH:16])=[O:15])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]Komponenten
Versuchsvorschrift
To an ice-cold stirred solution of ethyl 3-(3-(2-tert-butylphenoxy)azetidin-1-yl)-3-oxopropanoate (0.26 g, 0.81 mmol) in ethanol (10.0 mL) was added lithium hydroxide (2.44 ml of 1.0 M solution in water, 2.44 mmol) and the mixture was warmed at room temperature. After 2 h the reaction mixture was adjusted to about pH 1 with 1.0 M hydrochloric acid and concentrated under reduced pressure. The resulting residue was partitioned between ethyl acetate and water and separated. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The yellow residue was recrystallized from heptane/ethyl acetate to provide 3-(3-(2-tert-butylphenoxy)azetidin-1-yl)-3-oxopropanoic acid (0.12 g, 51%) as a white powder.
Aufarbeitung
- concentrationconcentrated under reduced pressure
- customThe resulting residue was partitioned between ethyl acetate and water
- customseparated
- washThe organic layer was washed with saturated sodium chloride
- dry with materialdried (Na2SO4)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe yellow residue was recrystallized from heptane/ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-b43413a286d44eb1a51d6c5c3d72b370
- Quelldatensatz
- uspto-grants-2013_11
- Patentnummer
- US08586571B2
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