1-Bromopropane → HCID 21707964, compound

HRID 651895Notes

Reaction equation

HRID 651895 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:7])[CH2:5][NH2:6].[CH2:8](Br)[CH2:9][CH3:10].C(N(C(C)C)CC)(C)C>C(#N)C>[CH2:8]([NH:6][CH2:5][C:4]([O:3][CH3:2])=[O:7])[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 78401-BromopropaneHCID 81531DiisopropylethylamineHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 21707964HCID 21707964, compoundYield 10.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of glycine methyl ester HCl (5.0 g, 39.8 mmol) in acetonitrile (100 mL) was treated with propyl bromide (3.7 mL, 39.8 mmol), and diisopropylethylamine (13.9 mL, 79.6 mmol). After stirring at room temperature for 1 hour, the mixture was heated at reflux overnight. Solution occurred at reflux temperature. The solvent was removed under reduced pressure and the residue triturated with Et2O/EtOAc. Filtering and removal of the solvent under pressure left 1.13 g of the crude product. Chromatography on silica gel, eluting with CHCl3/MeOH (98:2) gave 0.53 g (10.2% yield) of the product as a yellow oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureat reflux temperature
  4. customThe solvent was removed under reduced pressure
  5. customthe residue triturated with Et2O/EtOAc
  6. filtrationFiltering
  7. customremoval of the solvent under pressure
  8. waitleft 1.13 g of the crude product
  9. washChromatography on silica gel, eluting with CHCl3/MeOH (98:2)

Sources & evidence

ORD record
ord-4e42053e05184151ac037da8c6d99604
Source dataset
uspto-grants-2001_08
Patent number
US06281194B1

Reaction notes

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