HCID 69639922, compound → HCID 69639917, compound

HRID 251467Notes

Reaction equation

HRID 251467 reaction equation
[CH3:1][N:2]([N:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[N+:21]([O-])=O)[C:13]1=[O:24])[C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][C:6](=[O:8])[NH2:7]>CO.[Pd]>[CH3:1][N:2]([N:12]1[CH2:20][C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2[NH2:21])[C:13]1=[O:24])[C@H:3]([C:9]([OH:11])=[O:10])[CH2:4][CH2:5][C:6](=[O:8])[NH2:7]

Participants

4

Reactant 1

HCID 69639922HCID 69639922, compound

Product 1

HCID 69639917HCID 69639917, compoundYield 88,143.898%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of methyl N-(1-oxo-4-nitroisoindolin-2-yl)-L-glutamine (6.4 g, 0.02 mmol) and 5% Pd/C (0.6 g) in methanol (100 mL) was stirred under hydrogen (40 psi) at ambient temperature for two hours. The Pd catalyst was filtered off through a pad of Celite. After concentration of the filtrate, the resulting oily residue was triturated with MTBE (30 mL), which yielded a solid after standing at ambient temperature for one hour. The off-white solid was filtered, washed with MTBE (30 mL), and dried to furnish the title compound (5.4 g, 93% yield).

Workup

  1. filtrationThe Pd catalyst was filtered off through a pad of Celite
  2. customAfter concentration of the filtrate, the resulting oily residue was triturated with MTBE (30 mL), which
  3. customyielded a solid
  4. waitafter standing at ambient temperature for one hour
  5. filtrationThe off-white solid was filtered
  6. washwashed with MTBE (30 mL)
  7. customdried

Sources & evidence

ORD record
ord-80d5d95f9ef8481da40da67e51bc9fe2
Source dataset
uspto-grants-2011_01
Patent number
US07863451B2

Reaction notes

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