HCID 22997353, compound → HCID 22997334, compound

HRID 2296896Notes

Reaction equation

HRID 2296896 reaction equation
[N+:1]([C:4]1[CH:45]=[CH:44][C:7]([CH2:8][NH:9][C:10]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([C:23]3[CH:28]=[CH:27][C:26]([O:29][CH2:30][C:31]([NH:33][CH2:34][C:35]4[CH:40]=[CH:39][C:38]([N+:41]([O-])=O)=[CH:37][CH:36]=4)=[O:32])=[CH:25][CH:24]=3)([CH3:22])[CH3:21])=[CH:16][CH:15]=2)=[O:11])=[CH:6][CH:5]=1)([O-])=O>C1COCC1.[Pd]>[NH2:41][C:38]1[CH:37]=[CH:36][C:35]([CH2:34][NH:33][C:31]([CH2:30][O:29][C:26]2[CH:25]=[CH:24][C:23]([C:20]([C:17]3[CH:18]=[CH:19][C:14]([O:13][CH2:12][C:10]([NH:9][CH2:8][C:7]4[CH:6]=[CH:5][C:4]([NH2:1])=[CH:45][CH:44]=4)=[O:11])=[CH:15][CH:16]=3)([CH3:22])[CH3:21])=[CH:28][CH:27]=2)=[O:32])=[CH:40][CH:39]=1

Participants

4

Reactant 1

HCID 22997353HCID 22997353, compound

Product 1

HCID 22997334HCID 22997334, compoundYield 64.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

1.8 g of 2,2-bis-[4-(4-nitrobenzylamino)carbonylmethoxyphenyl]propane are dissolved in 300 ml of THF and, after addition of 0.5 g of palladium charcoal (10%), are hydrogenated in a bypass apparatus until the starting compound can no longer be detected (TLC). After the catalyst has been filtered off with suction, the filtrate is concentrated to dryness in vacuo and the residue is chromatographed through a silica gel column using a mixture of dichloromethane/ethanol, 95:5. The chromatographically pure fractions are combined and concentrated, and the residue is dried under high vacuum. 1.05 g of the title compound are obtained in the form of a solidified foam.

Workup

  1. filtrationAfter the catalyst has been filtered off with suction
  2. concentrationthe filtrate is concentrated to dryness in vacuo
  3. customthe residue is chromatographed through a silica gel column
  4. additiona mixture of dichloromethane/ethanol, 95:5
  5. concentrationconcentrated
  6. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-865bd977505544269f2163aa1edd80dc
Source dataset
uspto-grants-2002_12
Patent number
US06489327B1

Reaction notes

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