Lithium Hydroxide → HCID 59577007, compound

HRID 2041978Notes

Reaction equation

[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:18])[C:13]([O:15]CC)=[O:14])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>C(O)C>[C:1]([C:5]1[CH:22]=[CH:21][CH:20]=[CH:19][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:12](=[O:18])[C:13]([OH:15])=[O:14])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of ethyl 2-(3-(2-tert-butylphenoxy)azetidin-1-yl)-2-oxoacetate (1.65 g, 5.40 mmol) in ethanol (60.0 ml) was added lithium hydroxide (16.2 mL of 1.0 M solution in water, 16.2 mmol) at room temperature. After 1 h the reaction mixture was concentrated under reduced pressure, the resulting residue was diluted with water, cooled to 0° C., adjusted to about pH 1 with 1.0 N hydrochloric acid and the resulting solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered and concentrated under reduced pressure. The residue was recrystallized from heptane/ethyl acetate to provide 2-(3-(2-tert-butylphenoxy)azetidin-1-yl)-2-oxoacetic acid (0.97 g, 65%) as a white powder.

Workup

concentrationAfter 1 h the reaction mixture was concentrated under reduced pressure
additionthe resulting residue was diluted with water
extractionthe resulting solution was extracted with ethyl acetate
washThe organic layer was washed with saturated sodium chloride
dry with materialdried (Na2SO4)
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe residue was recrystallized from heptane/ethyl acetate

Sources & evidence

ORD record: ord-a5ad544785d34beb93db8da0dae66deb
Source dataset: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08586571B2

Reaction notes

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