Ethyl diazoacetate → HCID 54187262, compound

HRID 1085219Notes

Reaction equation

HRID 1085219 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-methylpyrrole 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-fe622a92f0af456185f06934cb436ace
Source dataset
uspto-grants-1991_04
Patent number
US05008290

Reaction notes

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