Ethyl bromoacetate → HCID 22708226, compound

HRID 1266513Notes

Reaction equation

HRID 1266513 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-dae3b1fbacf14c9b9f6214d838ce5bda
Source dataset
uspto-grants-2003_04
Patent number
US06548538B2

Reaction notes

Loading…