Acetonitrile → HCID 10635676, compound

HRID 1107375Notes

Reaction equation

HRID 1107375 reaction equation
[C:1]1([CH2:7][CH2:8]Br)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([O-:13])(O)=[O:11].[Na+].[C:15](#[N:17])C>>[C:1]1([CH2:7][CH2:8][NH:17][CH2:15][C:10]([O:13][CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 7666Phenethyl bromideHCID 516892Sodium Bicarbonate

Product 1

HCID 10635676HCID 10635676, compoundYield 38%

Procedure

A mixture of benzyl glycinate, p-toluenesulfonic acid salt (2.68 g, 7.94 mmol), (2-phenyl)bromoethane (0.98 g, 5.29 mmol), and solid NaHCO3 (1.56 g, 18.5 mmol) in acetonitrile (25 mL) were heated at reflux for 18 hour. The reaction was concentrated and diluted with EtOAc (25 mL). The organic solution was washed with H2O (25 mL) and brine (25 mL), dried (Na2SO4) and concentrated in vacuo. The residue was purified by elution through a pad of silica gel with a gradient mixture of hexane:EtOAc. The intermediate benzyl N-[(2-phenyl)ethyl]-glycinate (0.82 g) was obtained in 38% yield. Low Res MS: (M+H)+ =270.

Workup

  1. temperaturewere heated
  2. temperatureat reflux for 18 hour
  3. concentrationThe reaction was concentrated
  4. additiondiluted with EtOAc (25 mL)
  5. washThe organic solution was washed with H2O (25 mL) and brine (25 mL)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by elution through a pad of silica gel with a gradient mixture of hexane

Sources & evidence

ORD record
ord-8ac02376fd0348a1a29d45d25bd253db
Source dataset
uspto-grants-2000_05
Patent number
US06060462

Reaction notes

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