Ethyl diazoacetate → HCID 54187262, compound

HRID 1608166Notes

Reaction equation

HRID 1608166 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[N:15]([CH3:19])[CH:16]=[CH:17][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[N+](=[CH:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[N-]>C(Cl)CCl.[Cu]Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH2:12][CH2:13][C:14]2[N:15]([CH3:19])[C:16]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:17][CH:18]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 12192Ethyl diazoacetateHCID 14152354HCID 14152354, compound

Product 1

HCID 54187262HCID 54187262, compound

Reagents, catalysts & solvents 2

HCID 62652Cuprous chlorideCatalystHCID 111,2-DichloroethaneSolvent2×

Procedure

1.69 g of 2-(2-(4-fluorobenzenesulphonylamino)-ethyl)-1-methylpyrrol are dissolved in 6 ml of ethylene chloride and 0.06 g of copper(I)chloride are added. Under a nitrogen atmosphere the mixture is refluxed and then a solution of 0.34 g of ethyl diazoacetate in 6 ml of ethylene chloride is slowly added dropwise. After 20 minutes the evolution of nitrogen has ended and the suspension is concentrated to dryness by rotary evaporation. Then the residue is chromatographed over a silica gel column (ethylene chloride/ethyl acetate=100/1).

Workup

  1. temperatureUnder a nitrogen atmosphere the mixture is refluxed
  2. concentrationthe suspension is concentrated to dryness by rotary evaporation
  3. customThen the residue is chromatographed over a silica gel column (ethylene chloride/ethyl acetate=100/1)

Sources & evidence

ORD record
ord-1111d6b431f9401cb566dfde107a728a
Source dataset
uspto-grants-1989_09
Patent number
US04870076

Reaction notes

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