benzyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycinate → N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycine

HRID 534947Notes

Reaction equation

HRID 534947 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])[C:18]([NH:20][CH2:21][C:22]([O:24]CC2C=CC=CC=2)=[O:23])=[O:19])[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[CH2:12][CH2:13][N:14]([C:17](=[O:32])[C:18]([NH:20][CH2:21][C:22]([OH:24])=[O:23])=[O:19])[CH2:15][CH2:16]1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 66751166benzyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycinate

Product 1

HCID 66750891N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycineYield 98.2%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of benzyl N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycinate (Example 86, 350 mg, 0.80 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 N-{[4-(2-tert-butylphenyl)piperazin-1-yl](oxo)acetyl}glycine (0.273 g, 98%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-5f3657dd611d49928b1ba766a8430216
Source dataset
uspto-grants-2014_10
Patent number
US08853215B2

Reaction notes

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