Hydrochloric Acid → HCID 4290625, compound

HRID 278057Notes

Reaction equation

HRID 278057 reaction equation
[C:1](Cl)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].[NH2:19][CH:20]([C:22]([OH:24])=[O:23])[CH3:21].Cl>[OH-].[Na+]>[C:1]([NH:19][CH:20]([CH3:21])[C:22]([OH:24])=[O:23])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 602DL-alanineHCID 8206Palmitoyl chloride

Product 1

HCID 4290625HCID 4290625, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Conditions

Temperature
50 °C

Procedure

The compound may be prepared using the Schotten-Baumann procedure. Palmitoyl chloride (44.0 g, 0.16 mol) is added dropwise to a solution of DL-alanine (21.4 g, 0.24 mol) in 10% aqueous sodium hydroxide (200 ml) heated at 50° C. The pH of the reaction is monitored such that the pH does not drop below 10. After the addition is complete, the reaction is stirred for a further 1 hour before it is allowed to cool to room temperature and neutralised with concentrated hydrochloric acid. The resultant precipitate is collected by filtration, washed with water and allowed to dry in air. The product is recrystallised from ether-petrol to give 2-palmitoylaminoproprionic acid as a white solid (36.4 g, 70%).

Workup

  1. customThe compound may be prepared
  2. additionAfter the addition
  3. filtrationThe resultant precipitate is collected by filtration
  4. washwashed with water
  5. customto dry in air
  6. customThe product is recrystallised from ether-petrol

Sources & evidence

ORD record
ord-519eff6e63d84c0b9a33b3e4d2c77a39
Source dataset
uspto-grants-2002_03
Patent number
US06359008B1

Reaction notes

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