Hydrochloric Acid → HCID 66750892, compound

HRID 534934Notes

Reaction equation

HRID 534934 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:32])[CH2:18][CH:19]2[CH2:24][C:23](=[O:25])[N:22]([CH2:26][C:27]([O:29]C)=[O:28])[C:21](=[O:31])[CH2:20]2)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-:33].[Li+].Cl>C1COCC1>[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](=[O:32])[CH2:18][CH:19]([CH2:24][C:23]([NH:22][CH2:26][C:27]([OH:29])=[O:28])=[O:25])[CH2:20][C:21]([OH:33])=[O:31])[CH2:15][CH2:16]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66792847HCID 66792847, compound

Product 1

HCID 66750892HCID 66750892, compoundYield 108.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl (4-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}-2,6-dioxopiperidin-1-yl)acetate (Example 72, 0.463 g, 1.04 mmol) in THF (5 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 3 h the reaction mixture was acidified with 1 M hydrochloric acid solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, and the solvent was evaporated under reduced pressure to provide 5-[4-(2-tert-butylphenyl)piperazin-1-yl]-3-{2-[(carboxymethyl)amino]-2-oxoethyl}-5-oxopentanoic acid (0.505 g, quant) as a pale brown solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-cf01dce237074d3ab82937c75455030f
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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