Hydrochloric Acid → HCID 25262107, compound

HRID 2041997Notes

Reaction equation

HRID 2041997 reaction equation
[C:1]([C:5]1[CH:23]=[C:22]([Cl: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>C1COCC1>[C:1]([C:5]1[CH:23]=[C:22]([Cl: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 59577236HCID 59577236, compound

Product 1

HCID 25262107HCID 25262107, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-[3-(2-tert-butyl-4-chlorophenoxy)azetidin-1-yl]-4-oxobutanoate (236 mg, 0.67 mmol) obtained in Example 188 in THF (5.0 ml) was added lithium hydroxide (1.0M aqueous solution, 5.0 mL, 5.0 mmol) at room temperature. After 3 hr, the reaction mixture was adjusted to about pH 1 with 1.0N hydrochloric acid. The obtained solution was concentrated under reduced pressure, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride, dried (MgSO4), filtered, and concentrated under reduced pressure to give the title compound (222 mg, 98%) as a white solid.

Workup

  1. concentrationThe obtained solution was concentrated under reduced pressure
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium chloride
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-453d3aaf268e4cc8940e8cb1d4711fe9
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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