Succinic acid bis(3,4-dibenzyloxybenzylamide) → HCID 10383893, compound

HRID 339654Notes

Reaction equation

HRID 339654 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][C:46]=1[O:47]CC1C=CC=CC=1)[CH2:12][NH:13][C:14](=[O:43])[CH2:15][CH2:16][C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27]CC2C=CC=CC=2)=[C:23]([O:35]CC2C=CC=CC=2)[CH:22]=1)=[O:18])C1C=CC=CC=1.[H][H]>C1COCC1.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH:44]=[CH:45][C:46]=1[OH:47])[CH2:12][NH:13][C:14](=[O:43])[CH2:15][CH2:16][C:17]([NH:19][CH2:20][C:21]1[CH:26]=[CH:25][C:24]([OH:27])=[C:23]([OH:35])[CH:22]=1)=[O:18]

Participants

5

Reactant 2

HCID 57634450Succinic acid bis(3,4-dibenzyloxybenzylamide)HCID 178418361HCID 178418361, compound

Product 1

HCID 10383893HCID 10383893, compoundYield 13.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Succinic acid bis(3,4-dibenzyloxybenzylamide) (300 mg, 0.42 mmol) was dissolved in THF (50 ml) in a pressure bottle and warmed to 35 C to ensure dissolution of the solid. Palladium on carbon (50 mg 10% Pd/C) was added, and the vessel was pressurized with hydrogen (to 3 atm). The reaction was agitated for 1 hour at room temperature, whereupon TLC revealed reaction had gone to completion. The catalyst was removed by filtration, and the solvent removed under reduced pressure to afford DC-0067 as a crude solid (20 mg). This material was recrystallized from toluene and methanol to afford DC-0067.

Workup

  1. temperaturewarmed to 35 C
  2. dissolutiondissolution of the solid
  3. customreaction
  4. customThe catalyst was removed by filtration
  5. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-e90466e33838484c9930a35d4714f479
Source dataset
uspto-grants-2014_11
Patent number
US08895554B2

Reaction notes

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