Ethyl bromoacetate → HCID 22708226, compound

HRID 353179Notes

Reaction equation

HRID 353179 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][NH:7][CH2:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([S:16][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:12][CH:11]=1.Br[CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30].C(N(CC)CC)C.C(OCC)(=O)C>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>[CH2:32]([O:31][C:29](=[O:30])[CH2:28][N:7]([CH2:6][C:2]1[O:1][CH:5]=[CH:4][CH:3]=1)[CH2:8][CH2:9][C:10]1[CH:11]=[CH:12][C:13]([S:16][C:17]([CH3:26])([CH3:25])[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])=[CH:14][CH:15]=1)[CH3:33]

Participants

8

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 22708149HCID 22708149, compound

Product 1

HCID 22708226HCID 22708226, compoundYield 46.8%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.4 g of 1,1-dimethylethyl 2-[[4-[2-[(2-furanylmethyl)amino]ethyl]phenyl]thio]-2-methyl-propanoate, 1.5 g of ethyl bromoacetate, 0.97 g of triethylamine and 7.08 g of tetra-n-butylammonium iodide are dissolved in 100 ml of tetrahydrofuran and heated at reflux overnight. Ethyl acetate and water are added, and the mixture is extracted with water and sat. NaCl solution. Concentration and chromatography (petroleum ether/ethyl acetate 10+1) gives 1.38 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureat reflux overnight
  3. extractionthe mixture is extracted with water and sat. NaCl solution
  4. concentrationConcentration and chromatography (petroleum ether/ethyl acetate 10+1)

Sources & evidence

ORD record
ord-dd9b2cfda5654b0795e3f175d5569aab
Source dataset
uspto-grants-2004_06
Patent number
US06750236B2

Reaction notes

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