Ethylenediaminetetraacetic Acid → HCID 66858320, compound

HRID 1803156Notes

Reaction equation

HRID 1803156 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[NH:12][CH:13]=O.[CH2:15]([O:17][C:18](=[O:23])[CH2:19][NH:20][CH:21]=O)[CH3:16].C(N(CC)CC)C.O=P(Cl)(Cl)Cl.N1CCC[C@H]1C(O)=O.C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>ClCCl.C1COCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([N+:9]([O-:11])=[O:10])[CH:6]=[CH:5][C:4]=1[N:12]1[CH:13]=[C:19]([C:18]([O:17][CH2:15][CH3:16])=[O:23])[N:20]=[CH:21]1

Participants

9

Reactant 6

HCID 6049Ethylenediaminetetraacetic AcidHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 76615Glycine, N-formyl-, ethyl esterHCID 145742L-ProlineHCID 315885N-(2-methoxy-4-nitrophenyl)formamide

Product 1

HCID 66858320HCID 66858320, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Step N (1): Followed the method of R. Roy et. al Tetrahedron 2007, 63, 4912. To a solution of N-(2-methoxy-4-nitrophenyl)formamide (4.0 g, 28 mmol, U. Mario et. al General Pharmacology, 1979, 10, 309) and N-formylglycine ethyl ester (16.6 g, 153 mmol) in dichloromethane (20 mL) were added triethylamine (28 mL, 72 mmol) and POCl3 (8.0 mL, 200 mmol) dropwise at 0° C. The reaction was stirred at 0° C. for 2 h. The mixture was filtered over silica using dichloromethane/diethyl ether (4/1) and concentrated under reduced pressure. The crude residue was dissolved in THF (100 mL) to which Cu2O (400 mg, 2.8 mmol) and L-proline (644 mg, 5.6 mmol) were added and the resulting solution stirred at rt for 4 h. A solution of aq EDTA (5%) was added to the reaction mixture, which was then extracted with EtOAc. The crude residue was purified using silica gel column chromatography (EtOAc/dichloromethane) to afford ethyl 1-(2-methoxy-4-nitrophenyl)-1H-imidazole-4-carboxylate (2.0 g, 24% yield).

Workup

  1. filtrationThe mixture was filtered over silica
  2. concentrationconcentrated under reduced pressure
  3. additionwere added
  4. stirringthe resulting solution stirred at rt for 4 h
  5. extractionwas then extracted with EtOAc
  6. customThe crude residue was purified

Sources & evidence

ORD record
ord-d7f18b77a5b448dcbea79450ed142fc9
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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