HCID 59923450, compound → HCID 59923476, compound

HRID 2297723Notes

Reaction equation

HRID 2297723 reaction equation
[CH3:1][N:2]([CH3:34])[CH2:3][CH2:4][NH:5][C:6](=[O:33])[C@@H:7]([NH:18][C:19]([N:21]([CH2:30][CH2:31][OH:32])[CH2:22][CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:20])[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=1>C(O)C.[C].[Pd]>[NH2:15][C:12]1[CH:11]=[CH:10][C:9]([CH2:8][C@H:7]([NH:18][C:19]([N:21]([CH2:30][CH2:31][OH:32])[CH2:22][CH2:23][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[O:20])[C:6]([NH:5][CH2:4][CH2:3][N:2]([CH3:34])[CH3:1])=[O:33])=[CH:14][CH:13]=1

Participants

4

Reactant 1

HCID 59923450HCID 59923450, compound

Product 1

HCID 59923476HCID 59923476, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, 5% palladium-carbon (92 mg) is added to a solution of (2S)-N-[2-(dimethylamino)ethyl]-2-[3-(2-hydroxyethyl)-3-phenethylureido]-3-(4-nitrophenyl)propionamide (Compound No. 19-1, 921 mg) in ethanol (30 ml). The mixture is stirred under a hydrogen atmosphere for three hours. Palladium-carbon is filtered out with Celite, and the filtrate is concentrated under reduced pressure. The resulting oily matter is purified by silica gel column chromatography to give 418 mg (49%) of the titled compound (Compound No. 24-1) as noncrystalline powder.

Workup

  1. filtrationPalladium-carbon is filtered out with Celite
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customThe resulting oily matter is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-51ba3bbffd674a6fae3da47a8aab4e6f
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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