Hydrochloric Acid → HCID 66792755, compound

HRID 534993Notes

Reaction equation

HRID 534993 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](=[O:33])[C:18]([NH:20][C:21]2[CH:32]=[CH:31][C:24]([O:25][CH2:26][C:27]([O:29]C)=[O:28])=[CH:23][CH:22]=2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[Li+].[OH-].Cl>O1CCCC1>[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](=[O:33])[C:18]([NH:20][C:21]2[CH:22]=[CH:23][C:24]([O:25][CH2:26][C:27]([OH:29])=[O:28])=[CH:31][CH:32]=2)=[O:19])[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66792911HCID 66792911, compound

Product 1

HCID 66792755HCID 66792755, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl [4-({[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}amino)phenoxy]acetate (Example 200, 0.29 g, 0.64 mmol) and 1 M LiOH solution (5 mL, 5.0 mmol) in tetrahydrofuran (5 mL) was stirred at room temperature for 3 h. The reaction mixture was acidified with 1 M HCl solution and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was crystallized from diisopropyl ether to give the title compound (0.29 g, quant.) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-6cad416e3e4145b697af92182e887ce2
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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