Ethyl bromoacetate → HCID 20689154, compound

HRID 495965Notes

Reaction equation

HRID 495965 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[CH2:7][NH:8][C:9]3[CH:15]=[CH:14][CH:13]=[CH:12][C:10]=3[O:11][C:5]=2[CH:4]=1.[H-].[Na+].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>CS(C)=O>[CH2:25]([O:24][C:22](=[O:23])[CH2:21][N:8]1[CH2:7][C:6]2[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[CH:4][C:5]=2[O:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]1=2)[CH3:26]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 20689155HCID 20689155, compound

Product 1

HCID 20689154HCID 20689154, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 1-4 (2.04 g, 8.97 mmol) in DMSO (10 mL) was cooled to 0° C. and treated with sodium hydride (450 mg of 60% in oil, 11.2 mmol). The reaction mixture was warmed to room temperature for 15 min, followed by addition of ethyl bromoacetate (1.67 g, 10.0 mmol) and warming to 50° C. overnight. The solvent was removed in vacuo and the residue diluted with water and extracted with three portions of dichloromethane. The combined organic extracts were washed with brine and dried (Na2SO4). The solvent was removed in vacuo. Preparative centrifugal chromatography (SiO2, 6 mm, 50% EtOAc, 50% hexane) afforded 1-5.

Workup

  1. temperaturewarming to 50° C. overnight
  2. customThe solvent was removed in vacuo
  3. additionthe residue diluted with water
  4. extractionextracted with three portions of dichloromethane
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (Na2SO4)
  7. customThe solvent was removed in vacuo
  8. customPreparative centrifugal chromatography (SiO2, 6 mm, 50% EtOAc, 50% hexane) afforded 1-5

Sources & evidence

ORD record
ord-5d161423e80c4605ac1906c400a565ed
Source dataset
uspto-grants-2005_09
Patent number
US06943156B2

Reaction notes

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