HCID 57048546, compound → HCID 13456344, compound

HRID 1980286Notes

Reaction equation

HRID 1980286 reaction equation
[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([OH:15])=[O:14])[N:10]([C:16](=[O:39])[C@@H:17]([NH:19][C@H:20]([C:29]([O:31]CC2C=CC=CC=2)=[O:30])[CH2:21][CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH3:18])[C:9]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[H][H].[Pd]>[CH2:1]([N:8]1[CH2:12][C@@H:11]([C:13]([OH:15])=[O:14])[N:10]([C:16](=[O:39])[C@@H:17]([NH:19][C@H:20]([C:29]([OH:31])=[O:30])[CH2:21][CH2:22][C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH3:18])[C:9]1=[O:40])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 1

HCID 57048546HCID 57048546, compound

Product 1

HCID 13456344HCID 13456344, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

1.0 g of (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid is dissolved in 20 ml of methanol, and 50 mg of palladium black are added thereto. The mixture is shaken at room temperature in hydrogen gas atmosphere for two hours under an atmospheric pressure. Insoluble materials are filtered off, and the filtrate is concentrated under reduced pressure to remove solvent. The residue is triturated with ether, whereby 0.7 g of (4S)-1-benzyl-3-{(2S)-2-[N-((1S)-1-carboxy-3-phenylpropyl)amino]propionyl}-2-oxo-imidazolidine-4-carboxylic acid is obtained as colorless crystals. Yield: 83.9% The physico-chemical properties of this product are identical with those of the sample obtained in Example 8-(2).

Workup

  1. filtrationInsoluble materials are filtered off
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. customto remove solvent
  4. customThe residue is triturated with ether

Sources & evidence

ORD record
ord-cf46a25c8dc847eab2f1b15e826aed36
Source dataset
uspto-grants-1985_04
Patent number
US04508727

Reaction notes

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