Hydrochloric Acid → HCID 59577094, compound

HRID 2042000Notes

Reaction equation

HRID 2042000 reaction equation
[C:1]([C:5]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:6]=1[O:7][CH2:8][CH:9]1[CH2:12][N:11]([C:13](=[O:20])[CH2:14][C:15]([O:17]CC)=[O:16])[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C1COCC1>[C:1]([C:5]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:6]=1[O:7][CH2:8][CH:9]1[CH2:10][N:11]([C:13](=[O:20])[CH2:14][C:15]([OH:17])=[O:16])[CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59577322HCID 59577322, compound

Product 1

HCID 59577094HCID 59577094, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl 3-{3-[(2-tert-butyl-4-chlorophenoxy)methyl]azetidin-1-yl}-3-oxopropanoate (285 mg, 0.78 mmol) obtained in Example 208 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 (203 mg, 77%) 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-c6f9613a18c64bef965cc144050fd04b
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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