Docosanoic Acid → HCID 24985706, compound

HRID 1454017Notes

Reaction equation

HRID 1454017 reaction equation
[Cl-].[Ca+2].[Cl-].C(Br)(=O)C.[CH3:8][N:9]([C:13]([NH2:15])=[NH:14])[CH2:10][CH2:11][OH:12].[C:16](O)(=[O:38])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(Cl)Cl>[C:16]([O:12][CH2:11][CH2:10][N:9]([CH3:8])[C:13]([NH2:15])=[NH:14])(=[O:38])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

Participants

6

Reactant 4

HCID 8215Docosanoic AcidHCID 10482Acetyl bromide2×HCID 83440N-(2-Hydroxyethyl)-N-methylguanidine2×HCID 5284359Calcium Chloride

Product 1

HCID 24985706HCID 24985706, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

In a dry 3-necked round bottomed flask, containing a magnetic stirrer, equipped with a dropping funnel, a reflux condenser protected from moisture by a calcium chloride filled drying tube and a rubber septum. The dropping funnel is filled with 12.73 mL (150 mmol) of acetyl bromide and 35 mL of dry DCM. The flask is charged with 35.14 g (300 mmol) of Creatinol and 150 mL of dry DCM, and cooled with an ice-water bath to about 0° C., under a nitrogen atmosphere. The acetyl bromide solution is then added slowly with stirring, over a period of 10 minutes, to the Creatinol solution. The solution is stirred for another 15 minutes, after which 23.84 g (70 mmol) of Docosanoic acid is added in one portion and the reaction is slowly heated to about 65° C. for about 12 hours. Then the solution is allowed to cool to room temperature, after which the solvent is removed under reduced pressure to yield the crude ester. The crude ester is then purified by flash chromatography (ethyl acetate/hexanes; 1/3) to yield pure 2-(1-methylguanidino)ethyl docosanoate.

Workup

  1. additionIn a dry 3-necked round bottomed flask, containing a magnetic stirrer
  2. customequipped with a dropping funnel, a reflux condenser
  3. additionfilled
  4. customdrying tube
  5. temperaturethe reaction is slowly heated to about 65° C. for about 12 hours
  6. temperatureto cool to room temperature
  7. customafter which the solvent is removed under reduced pressure
  8. customto yield the crude ester
  9. customThe crude ester is then purified by flash chromatography (ethyl acetate/hexanes; 1/3)

Sources & evidence

ORD record
ord-e72c7c26c1444f85ab80bc243c0b89f3
Source dataset
uspto-grants-2009_01
Patent number
US07476749B1

Reaction notes

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