Glycine → NoName_600

HRID 400216Notes

Reaction equation

HRID 400216 reaction equation
[OH-].[Na+].[NH2:3][CH2:4][C:5]([OH:7])=[O:6].[CH2:8](Br)[CH2:9][CH2:10][CH3:11]>CO.O>[CH2:8]([NH:3][CH2:4][C:5]([OH:7])=[O:6])[CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 3

HCID 750GlycineHCID 8002Butyl bromideHCID 14798Sodium Hydroxide

Product 1

HCID 413376NoName_600Yield 41.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A! A 32% solution of sodium hydroxide (123 ml) was added to a mixture of glycin (50 g, 0.66 mole) and butyl bromide (75 ml, 0.66 mole) in methanol (600 ml) and water (600 ml), the reaction mixture was refluxed for 24 hours, then the solvend was evaporated under vacuum. The crude was dissolved in ethanol, the salts were filtered off 3 times, and the solvent was evaporated under vacuum. The resulting crude was purified by flash chromatography (eluent: chloroform/methanol/concentrated ammonia 6:4:0.5) yielding 36 g of N-butyl-glycine.

Workup

  1. temperaturethe reaction mixture was refluxed for 24 hours
  2. customthe solvend was evaporated under vacuum
  3. dissolutionThe crude was dissolved in ethanol
  4. filtrationthe salts were filtered off 3 times
  5. customthe solvent was evaporated under vacuum
  6. customThe resulting crude was purified by flash chromatography (eluent: chloroform/methanol/concentrated ammonia 6:4:0.5)

Sources & evidence

ORD record
ord-a3d5ec9ea0704424bf0b88f5323cba0a
Source dataset
uspto-grants-1998_10
Patent number
US05827881

Reaction notes

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