HCID 66751246, compound → HCID 66792797, compound

HRID 534940Notes

Reaction equation

HRID 534940 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]([O:29]CC3C=CC=CC=3)=[O:28])[C:21](=[O:37])[CH2:20]2)[CH2:13][CH2:12]1)([CH3:4])([CH3:3])[CH3:2]>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[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]([OH:29])=[O:28])[C:21](=[O:37])[CH2:20]2)[CH2:13][CH2:12]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66751246HCID 66751246, compound

Product 1

HCID 66792797HCID 66792797, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of benzyl (4-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}-2,6-dioxopiperidin-1-yl)acetate (Example 78, 0.28 g, 0.539 mmol) and palladium hydroxide (20% on carbon, wetted with ca. 50% water, 30 mg) in ethyl acetate (25 mL) was stirred under hydrogen atmosphere at room temperature for 3 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to provide (4-{2-[4-(2-tert-butylphenyl)piperazin-1-yl]-2-oxoethyl}-2,6-dioxopiperidin-1-yl)acetic acid (0.21 g, 91%) as a white powder.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-aa93da51d1b34c959d9223cd23a0be6b
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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