Hydrochloric Acid → HCID 66751043, compound

HRID 534936Notes

Reaction equation

HRID 534936 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:38])[CH2:18][CH:19]2[CH2:24][C:23](=[O:25])[N:22]([CH2:26][C:27]3[CH:36]=[CH:35][C:30]([C:31]([O:33]C)=[O:32])=[CH:29][CH:28]=3)[C:21](=[O:37])[CH2:20]2)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2].[OH-:39].[Li+].Cl>C1COCC1>[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:38])[CH2:18][CH:19]([CH2:24][C:23]([OH:25])=[O:39])[CH2:20][C:21]([NH:22][CH2:26][C:27]2[CH:28]=[CH:29][C:30]([C:31]([OH:33])=[O:32])=[CH:35][CH:36]=2)=[O:37])[CH2:13][CH2:12]1)([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 66792734HCID 66792734, compound

Product 1

HCID 66751043HCID 66751043, compoundYield 104.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of methyl 4-[(4-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}-2,6-dioxopiperidin-1-yl)methyl]benzoate (Example 74, 0.575 g, 1.11 mmol) in THF (5 mL) stirring at 0° C. was added 1 M lithium hydroxide solution (5 mL, 5 mmol). After 1 h the reaction mixture was warmed to room temperature and kept stirring for 3 h. The 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 the crude product. The product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 20:80) to provide 4-[({5-[4-(2-tert-butylphenyl)piperazin-1-yl]-3-(carboxymethyl)-5-oxopentanoyl}amino)methyl]benzoic acid (0.608 g, quant) as a white 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
  5. customto provide the crude product
  6. customThe product was purified by flash column chromatography (silica gel, n-hexane/ethyl acetate=90:10 to 20:80)

Sources & evidence

ORD record
ord-b0dbe56199a24b16914dd2a9372ed171
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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