Hydrochloric Acid → HCID 59577023, compound

HRID 2041989Notes

Reaction equation

HRID 2041989 reaction equation
[C:1]([C:5]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:19])[CH2:13][CH2:14][C:15]([O:17]C)=[O:16])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>CO>[C:1]([C:5]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:19])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59577312HCID 59577312, compound

Product 1

HCID 59577023HCID 59577023, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-[3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-yl]-4-oxobutanoate (214 mg, 0.63 mmol) obtained in Example 79 in methanol (6.0 mL) was added lithium hydroxide (1.0M aqueous solution, 1.9 mL, 1.9 mmol) at 0° C. The reaction mixture was warmed to room temperature, and stirred for 1 h. After cooling to 0° C., the mixture was adjusted to about pH 1 with 1.0N hydrochloric acid. The obtained solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried (Na2SO4), filtered, and concentrated under reduced pressure to give 4-[3-(2-tert-butyl-4-fluorophenoxy)azetidin-1-yl]-4-oxobutanoic acid (0.19 g, 92%) as a white powder.

Workup

  1. temperatureAfter cooling to 0° C.
  2. extractionThe obtained solution was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ac41ff36836b471783323be331510287
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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