1,2-Dichloroethane → HCID 69743184, compound

HRID 1760365Notes

Reaction equation

HRID 1760365 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:28]([O:30][CH2:31][CH3:32])=[O:29])[CH2:10][CH2:9][C:8](=[O:11])[N:7]1[C:12]1[CH:13]=[N:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:27])=O)=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)=[O:5])[CH3:2].O.O[N:35]1C2C=CC=CC=2N=[N:36]1.ClCCCl.C(Cl)Cl>C(OCC)(=O)C>[CH2:31]([O:30][C:28]([C:6]1([C:4]([O:3][CH2:1][CH3:2])=[O:5])[CH2:10][CH2:9][C:8](=[O:11])[N:7]1[C:12]1[CH:13]=[N:14][C:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([NH:35][NH2:36])=[O:27])=[CH:21][CH:20]=2)=[CH:16][CH:17]=1)=[O:29])[CH3:32]

Participants

6

Reactant 4

HCID 111,2-DichloroethaneHCID 6344DichloromethaneHCID 27960291-Hydroxybenzotriazole hydrateHCID 69743182HCID 69743182, compound

Product 1

HCID 69743184HCID 69743184, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of affording 1-[6-(4-Carboxy-phenoxy)-pyridin-3-yl]-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.4 g, 0.97 mmol), 1-hydroxybenzotriazole hydrate (0.176 g, 1.3 mmol), 1,2-dichloroethane (0.25 g, 1.3 mmol) and 6 mL of methylene chloride was stirred at room temperature for 20 minutes. The mixture was treated with boc-hydrazide (0.17 g, 1.3 mmol) and stirred at room temperature overnight. The mixture was diluted with ethyl acetate, washed with 1M hydrochloric acid, sodium bicarbonate solution, brine, dried over sodium sulphate, filtered and concentrated in vacuo. The residue was dissolved in 5 mL of 1:1 V/V methylene chloride-trifluoroacetic acid, stirred for 1 hours at ambient temperature and was concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with 1M sodium hydroxide, brine, dried over sodium sulphate, filtered and concentrated, affording 1-[6-(4-Hydrazinocarbonyl-phenoxy)-pyridin-3-yl]-5-oxo-pyrrolidine-2,2-dicarboxylic acid diethyl ester (0.20 g) as a colorless syrup. HPLC: 2.770 min.

Workup

  1. stirringstirred at room temperature overnight
  2. washwashed with 1M hydrochloric acid, sodium bicarbonate solution, brine
  3. dry with materialdried over sodium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. dissolutionThe residue was dissolved in 5 mL of 1
  7. stirring1 V/V methylene chloride-trifluoroacetic acid, stirred for 1 hours at ambient temperature
  8. concentrationwas concentrated in vacuo
  9. dissolutionThe residue was dissolved in ethyl acetate
  10. washwashed with 1M sodium hydroxide, brine
  11. dry with materialdried over sodium sulphate
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-759a8dd524cb49248e4c4be0fc5e50f4
Source dataset
uspto-grants-2005_01
Patent number
US06841671B2

Reaction notes

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