Hydrochloric Acid → HCID 66792826, compound

HRID 534926Notes

Reaction equation

HRID 534926 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:16][CH2:15][N:14]([C:17]([CH:19]2[CH2:23][CH2:22][C:21](=[O:24])[N:20]2[CH2:25][C:26]([O:28]C)=[O:27])=[O:18])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+].Cl>CO>[C:1]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N:11]1[CH2:12][CH2:13][N:14]([C:17]([CH:19]2[CH2:23][CH2:22][C:21](=[O:24])[N:20]2[CH2:25][C:26]([OH:28])=[O:27])=[O:18])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66792833HCID 66792833, compound

Product 1

HCID 66792826HCID 66792826, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirring solution of methyl (2-{[4-(2-tert-butylphenyl)piperazin-1-yl]carbonyl}-5-oxopyrrolidin-1-yl)acetate obtained in Example 64 (0.39 g, 0.97 mmol) in methanol (12 mL) was added 1 M lithium hydroxide (2.9 mmol, 2.9 mL) and the mixture was stirred at room temperature for 1 h. The reaction mixture was acidified with 1 M hydrochloric acid (pH 3) and concentrated under reduced pressure. The resulting residue was partitioned between ethyl acetate and water, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting solid was recrystallized from hexane-diethyl ether to give the title compound (0.24 g, 64%) as a white solid, mp 273° C.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe resulting residue was partitioned between ethyl acetate and water
  3. washthe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting solid was recrystallized from hexane-diethyl ether

Sources & evidence

ORD record
ord-0cd458175adf49f19ec30532f4e2d9ea
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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