Hydrochloric Acid → N-Palmitoylglycine

HRID 709327Notes

Reaction equation

HRID 709327 reaction equation
[NH2:1][CH2:2][C:3]([OH:5])=[O:4].[OH-].[Na+].[C:8](Cl)(=[O:24])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23].Cl>O.C(O)(C)C>[NH:1]([C:8]([CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:24])[CH2:2][C:3]([OH:5])=[O:4]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 8206Palmitoyl chlorideHCID 14798Sodium Hydroxide

Product 1

HCID 151008N-PalmitoylglycineYield 32%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

First, 27.3 g (364 mmol) of glycine and 29.1 g (727 mmol) of sodium hydroxide were dissolved in a mixed solvent of 450 g composed of i-propanol and 200 g of water under stirring at room temperature, then cooled to 10° C. Next, 100 g (364 mmol) of palmitic acid chloride was added dropwise thereto over a period of 1 hour. The reaction product was returned to room temperature, then stirred for about 15 hours. Next, 400 g of water was added thereto, following which 73.8 g (727 mmol) of 35% hydrochloric acid was added dropwise. The solid that deposited out was recovered, slurry washed, and purified by re-crystallization from methanol, giving 36.4 g (yield, 32%) of N-palmitoyl-Gly as a white solid.

Workup

  1. temperaturecooled to 10° C
  2. customwas returned to room temperature
  3. stirringstirred for about 15 hours
  4. additionwas added dropwise
  5. customThe solid that deposited out was recovered
  6. washslurry washed
  7. custompurified by re-crystallization from methanol

Sources & evidence

ORD record
ord-5f388309885741abab1fbb30ae32d001
Source dataset
uspto-grants-2015_11
Patent number
US09180201B2

Reaction notes

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