Methanol → HCID 59927749, compound

HRID 2297722Notes

Reaction equation

HRID 2297722 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH2:33][CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:5](=[O:32])[NH:6][C@@H:7]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([O:24]CC2C=CC=CC=2)=[CH:20][CH:19]=1)[C:8]([N:10]1[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]1)=[O:9].CO>O1CCCC1.[OH-].[OH-].[Pd+2]>[OH:1][CH2:2][CH2:3][N:4]([CH2:33][CH2:34][C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)[C:5](=[O:32])[NH:6][C@@H:7]([CH2:17][C:18]1[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=1)[C:8]([N:10]1[CH2:11][CH2:12][N:13]([CH3:16])[CH2:14][CH2:15]1)=[O:9]

Participants

5

Reactant 2

HCID 887MethanolHCID 69930486HCID 69930486, compound

Product 1

HCID 59927749HCID 59927749, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Under a nitrogen atmosphere, 20% palladium hydroxide on carbon (200 mg) is added to a solution of 1-[(2S)-2-[3-(2-hydroxyethyl)-3-phenethylureido]-3-[4-(benzyloxy)phenyl]propionyl]-4-methylpiperazine (Compound No. 18-40, 1.09 g) in tetrahydrofuran (2 ml)-methanol (2 ml). The mixture is stirred under a hydrogen atmosphere for three days. Palladium hydroxide on carbon is filtered out with Celite, and the filtrate is concentrated under reduced pressure to give 685 mg (75%) of the titled compound (Compound No. 23-1) as noncrystalline powder.

Workup

  1. filtrationPalladium hydroxide on carbon is filtered out with Celite
  2. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-b61e3811dbed4b689a272e3caf92645a
Source dataset
uspto-grants-2002_12
Patent number
US06492370B1

Reaction notes

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