Hydrochloric Acid → HCID 25242543, compound

HRID 2041982Notes

Reaction equation

HRID 2041982 reaction equation
[C:1]([C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[O:7][CH:8]1[CH2:11][N:10]([C:12](=[O:20])[CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])[CH2:9]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>C(O)C>[C:1]([C:5]1[CH:24]=[CH:23][CH:22]=[CH:21][C:6]=1[O:7][CH:8]1[CH2:9][N:10]([C:12](=[O:20])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])[CH2:11]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 59577031Ethyl 4-(3-(2-tert-butylphenoxy)azetidin-1-yl)-4-oxobutanoate

Product 1

HCID 25242543HCID 25242543, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-(3-(2-tert-butylphenoxy)azetidin-1-yl)-4-oxobutanoate (0.47 g, 1.41 mmol) obtained in Example 11 in ethanol (20.0 mL) was added lithium hydroxide (1.0M aqueous solution, 4.23 ml, 4.23 mmol) under ice-cooling, and the mixture was stirred at room temperature. After 2 hr, the reaction mixture was adjusted to about pH 1 with 1.0M hydrochloric acid, and the mixture was concentrated under reduced pressure. The obtained residue was partitioned to between ethyl acetate and water, and 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 give the title compound (0.28 g, 65%) as a white powder.

Workup

  1. temperaturecooling
  2. concentrationthe mixture was concentrated under reduced pressure
  3. customThe obtained residue was partitioned to between ethyl acetate and water
  4. washthe organic layer was washed with saturated sodium chloride
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was recrystallized from heptane/ethyl acetate

Sources & evidence

ORD record
ord-f95966de11014e5f929bc1769f1890b2
Source dataset
uspto-grants-2013_11
Patent number
US08586571B2

Reaction notes

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