Dimethylformamide → HCID 18695430, compound

HRID 1870217Notes

Reaction equation

HRID 1870217 reaction equation
[F:1][C:2]1[CH:19]=[C:18](F)[C:17]([N+:21]([O-:23])=[O:22])=[CH:16][C:3]=1[O:4][C:5]1[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=1.Cl.[CH2:25]([O:27][C:28](=[O:31])[CH2:29][NH2:30])[CH3:26].C1COCC1.CN(C=O)C>C(OCC)(=O)C.C(N(CC)CC)C>[CH2:25]([O:27][C:28](=[O:31])[CH2:29][NH:30][C:18]1[CH:19]=[C:2]([F:1])[C:3]([O:4][C:5]2[CH:15]=[CH:14][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[CH:7][CH:6]=2)=[CH:16][C:17]=1[N+:21]([O-:23])=[O:22])[CH3:26]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 2723640Glycine ethyl ester, hydrochlorideHCID 18695462HCID 18695462, compound

Product 1

HCID 18695430HCID 18695430, compoundYield 61%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2.38 g (7.36 mmol) of ethyl 4-(2,4-difluoro-5-nitrophenoxy)benzoate, 1.03 g of glycine ethyl ester hydrochloride, 30 ml of THF, 10 ml of DMF and 2.06 ml of triethylamine was subjected to heating under reflux for 10 hours. After cooling, the reaction mixture was diluted with ethyl acetate. The insoluble matter was removed by filtration and the filtrate was concentrated under reduced pressure. The resulting residue was dissolved in ethyl acetate. The resulting solution was washed successively with water and brine, dried over anhydrous sodium sulfate and then, concentrated under reduced pressure. The resulting residue was purified by chromatography on a silica gel column (developing solvent: hexane:dichloromethane:ethyl acetate=8:2:1) to give 1.81 g (61%) of N-[4-(4-ethoxycarbonylphenoxy)-5-fluoro-2-nitrophenyl]glycine ethyl ester.

Workup

  1. temperatureto heating
  2. temperatureunder reflux for 10 hours
  3. temperatureAfter cooling
  4. customThe insoluble matter was removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in ethyl acetate
  7. washThe resulting solution was washed successively with water and brine
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by chromatography on a silica gel column (developing solvent: hexane:dichloromethane:ethyl acetate=8:2:1)

Sources & evidence

ORD record
ord-89092a62ae5840ac9146a68363ad5288
Source dataset
uspto-grants-2000_08
Patent number
US06096743

Reaction notes

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