Water → HCID 86747852, compound

HRID 1590700Notes

Reaction equation

HRID 1590700 reaction equation
CN(C)CCCN=C=NCC.[O:12]=[C:13]1[CH:17]=[CH:16][C:15](=[O:18])[N:14]1[CH:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([OH:22])=O.[Cl:27][C:28]1[CH:29]=[C:30]([CH:32]=[C:33]([Cl:35])[CH:34]=1)[NH2:31].O>O1CCCC1.CCCCCC.C(OCC)(=O)C>[O:18]=[C:15]1[CH:16]=[CH:17][C:13](=[O:12])[N:14]1[CH:19]([CH2:23][CH:24]([CH3:26])[CH3:25])[C:20]([NH:31][C:30]1[CH:29]=[C:28]([Cl:27])[CH:34]=[C:33]([Cl:35])[CH:32]=1)=[O:22]

Participants

7

Reactant 4

HCID 962WaterHCID 122813,5-DichloroanilineHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 3199392-(2,5-dioxopyrrol-1-yl)-4-methylpentanoic acid

Product 1

HCID 86747852HCID 86747852, compoundYield 16.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

1-(3-Dimethylaminopropyl)-3-ethyl-carbodiimide (3.5 g, 0.0182 mol) is added to a suspension of DL-2,5-dioxo-α-isobutyl-3-pyrroline-1-acetic acid (3.5 g, 0.0166 mol) in tetrahydrofuran. The reaction mixture is stirred for 30 minutes, treated with 3,5-dichloroaniline (2.69 g, 0.0166 mol) under nitrogen, stirred at room temperature for 12 hours and poured into water. The mixture is extracted with methylene chloride. The extracts are combined and concentrated in vacuo to give a residue. Flash chromatography using hexane/ethyl acetate (80/20) as eluent on silica gel of the residue yields the title compound as a pale yellow solid (0.97 g, 16%, mp 150.5° C.), identified by 1HNMR CIMS and IR analysis.

Workup

  1. stirringstirred at room temperature for 12 hours
  2. extractionThe mixture is extracted with methylene chloride
  3. concentrationconcentrated in vacuo
  4. customto give a residue

Sources & evidence

ORD record
ord-8f3579da9527499bb86f65b618ed4105
Source dataset
uspto-grants-1993_04
Patent number
US05204366

Reaction notes

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