Hydrochloric Acid → Glycine

HRID 1954471Notes

Reaction equation

HRID 1954471 reaction equation
C(CC[NH:6][CH2:7][C:8]([O-:10])=[O:9])(O)=O.[Na+].[Na+].[C:13]([CH2:16][CH2:17][NH:18][CH2:19][C:20]([O-:22])=[O:21])([OH:15])=[O:14].[C:23](Cl)(=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34].[OH-].[Na+].Cl>CC(C)=O>[NH2:6][CH2:7][C:8]([OH:10])=[O:9].[C:13]([CH2:16][CH2:17][N:18]([C:23](=[O:35])[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH2:19][C:20]([OH:22])=[O:21])([OH:15])=[O:14]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8166Dodecanoyl chlorideHCID 14798Sodium HydroxideHCID 86755850HCID 86755850, compound

Product 2

HCID 750GlycineHCID 10882059HCID 10882059, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
17.5 °C

Procedure

150 ml of acetone was added to the aqueous solution of disodium N-carboxyethylglycinate obtained in Example 7 while continuously stirring. Then, 228.29 g (1.0435 mol) of dodecanoyl chloride was dropwise added to this solution over a period of 1.5 hours while stirring. During this period, the reaction system was maintained at a pH of from 9 to 11 by dropwise adding a 40% aqueous solution of NaOH while the temperature was maintained at 10 to 25° C. After the completion of the dropwise addition, the reaction mixture was stirred at room temperature for 2 hours. Thereafter, the pH of the reaction mixture was adjusted to 1.2 with concentrated hydrochloric acid. A formed white precipitate was separated by filtration, washed with water and dried to thereby give 324.71 g (yield from glycine: 92.5%) of a white powder of N-carboxyethyl-N-dodecanoylglycine. The infrared absorption spectrum, 1H-NMR spectrum, mass spectrum, and results of elemental analysis thereof were the same as those obtained in Example 6.

Workup

  1. stirringwhile stirring
  2. waitDuring this period
  3. temperaturethe reaction system was maintained at a pH of from 9 to 11
  4. additionAfter the completion of the dropwise addition
  5. stirringthe reaction mixture was stirred at room temperature for 2 hours
  6. customA formed white precipitate was separated by filtration
  7. washwashed with water
  8. customdried
  9. customto thereby give

Sources & evidence

ORD record
ord-c5a6fb8e1d4745be821922de85f65d0c
Source dataset
uspto-grants-2000_09
Patent number
US06121470

Reaction notes

Loading…