HCID 59238173, compound → HCID 59238167, compound

HRID 2068568Notes

Reaction equation

HRID 2068568 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-])=O)=[C:16]([C:23](=[O:39])[NH:24][CH:25]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:26][O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[CH:19]=[CH:18][C:17]([NH2:20])=[C:16]([C:23](=[O:39])[NH:24][CH:25]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:26][O:27][C:28]([CH3:29])([CH3:31])[CH3:30])[CH:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 59238173HCID 59238173, compound

Product 1

HCID 59238167HCID 59238167, compoundYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

4-[3-(2-tert-Butoxy-1-tert-butoxycarbonyl-ethylcarbamoyl)-4-nitro-phenyl]-piperazine-1-carboxylic acid tert-butyl ester (10 g) was dissolved in 250 mL of methanol. This solution was treated with 1.2 g of 10% (wt/wt) palladium on carbon catalyst under nitrogen atmosphere. The mixture was then degassed before stirring under 1 atmosphere of hydrogen gas at room temperature for approximately 2.5 hours. At this time, the reaction mixture was filtered through celite and washed with copious volumes of methanol. The dark filtrate was concentrated in vacuo and the residue was further dried over phosphorous pentaoxide. In this manner, 9.49 g of the expected product was obtained as a grey-purple solid. H1-NMR spectroscopy indicated a spectrum consistent with 4-[4-amino-3-(2-tert-butoxy-1-tert-butoxycarbonyl-ethylcarbamoyl)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe mixture was then degassed
  2. filtrationAt this time, the reaction mixture was filtered through celite
  3. washwashed with copious volumes of methanol
  4. concentrationThe dark filtrate was concentrated in vacuo
  5. customthe residue was further dried over phosphorous pentaoxide

Sources & evidence

ORD record
ord-3f9d7d1fa4924280bc76778ebe97cfc7
Source dataset
uspto-grants-2012_10
Patent number
US08299023B2

Reaction notes

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