HCID 70126829, compound → HCID 70005271, compound

HRID 993239Notes

Reaction equation

HRID 993239 reaction equation
[C:1]([O:5][C:6](=[O:45])[CH2:7][CH:8]([NH:17][CH2:18][CH2:19][N:20](C(OCC1C=CC=CC=1)=O)[CH2:21][CH:22]=[CH:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)[N:25]=1)[C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>CCO.[Pd]>[C:1]([O:5][C:6](=[O:45])[CH2:7][CH:8]([NH:17][CH2:18][CH2:19][NH:20][CH2:21][CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([NH:30][CH2:31][CH:32]2[CH2:34][CH2:33]2)[N:25]=1)[C:9]1[CH:10]=[N:11][C:12]([O:15][CH3:16])=[CH:13][CH:14]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 70126829HCID 70126829, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 70005271HCID 70005271, compoundYield 57.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 2-6 (29.0 g, 47.0 mmol) and 10% Pd/C (7.25 g) in EtOH (500 mL) was stirred under a balloon of hydrogen for 18 h. Filtration through celite and evaporative removal of the solvent followed by purification on silica gel (90:10:1 CHCl3:MeOH:NHOH) afforded 13 g of 2-7.

Workup

  1. filtrationFiltration through celite
  2. customremoval of the solvent
  3. customfollowed by purification on silica gel (90:10:1 CHCl3:MeOH:NHOH)

Sources & evidence

ORD record
ord-72d762822b104f2a90b1c56e415d9688
Source dataset
uspto-grants-2002_10
Patent number
US06472403B2

Reaction notes

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