Hydrochloric Acid → HCID 25262259, compound

HRID 2041999Notes

Reaction equation

HRID 2041999 reaction equation
[C:1]([C:5]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:6]=1[O:7][CH2:8][CH:9]1[CH2:12][N:11]([C:13](=[O:18])[C:14]([O:16]C)=[O:15])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:22]=[C:21]([Cl:23])[CH:20]=[CH:19][C:6]=1[O:7][CH2:8][CH:9]1[CH2:10][N:11]([C:13](=[O:18])[C:14]([OH:16])=[O:15])[CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59577091HCID 59577091, compound

Product 1

HCID 25262259HCID 25262259, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of methyl {3-[(2-tert-butyl-4-chlorophenoxy)methyl]azetidin-1-yl}(oxo)acetate (232 mg, 0.68 mmol) obtained in Example 206 in THF (5.0 mL) was added lithium hydroxide (1.0M aqueous solution, 5.0 mL, 5.0 mmol) at 0° C. After stirring at 0° C. for 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 (214 mg, 96%) 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-8e875fd39f004cc48b77018c018e5da4
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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