Glycine → 2-(2-propylpentanoylamino)acetic Acid

HRID 728613Notes

Reaction equation

HRID 728613 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[CH2:6]([CH:9]([CH2:13][CH2:14][CH3:15])[C:10](Cl)=[O:11])[CH2:7][CH3:8].[OH-].[Na+]>O>[CH2:6]([CH:9]([CH2:13][CH2:14][CH3:15])[C:10]([NH:1][CH2:2][C:3]([OH:5])=[O:4])=[O:11])[CH2:7][CH3:8]

Participants

5

Reactant 3

HCID 750GlycineHCID 14798Sodium HydroxideHCID 762402-Propylvaleryl chloride

Product 1

HCID 1819192-(2-propylpentanoylamino)acetic AcidYield 59%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In 63 ml of water was dissolved 6.93 g of glycine, and under ice-cooling, 15 g of 2-n-propyl-n-pentanoyl chloride and 13 ml of a 36% sodium hydroxide solution were alternately added dropwise. After completion of the dropwise addition, the mixture was stirred at room temperature for 3 hours to conduct the reaction, adjusted a pH thereof to about 2 with a 1 N hydrochloric acid, and precipitated crystals were collected by filtration. The crystals were dissolved in ethyl acetate, washed with a saturated saline solution and then dried over anhydrous magnesium sulfate. Crystals obtained by condensing the solvent under reduced pressure were recrystallized from hexane-ethyl acetate to give 10.9 g (Yield: 59%) of the title compound as colorless needle crystals.

Workup

  1. temperatureunder ice-cooling
  2. additionAfter completion of the dropwise addition
  3. customthe reaction
  4. customto about 2 with a 1 N hydrochloric acid, and precipitated crystals
  5. filtrationwere collected by filtration
  6. dissolutionThe crystals were dissolved in ethyl acetate
  7. washwashed with a saturated saline solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customCrystals obtained by condensing the solvent under reduced pressure
  10. customwere recrystallized from hexane-ethyl acetate

Sources & evidence

ORD record
ord-0d27a10e0d914d9f943eaf6d8fe33c3d
Source dataset
uspto-grants-1991_09
Patent number
US05049551

Reaction notes

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