Octanoic Acid → HCID 24985708, compound

HRID 1454014Notes

Reaction equation

HRID 1454014 reaction equation
[Cl-].[Ca+2].[Cl-].C(Cl)(=O)C.[CH3:8][N:9]([C:13]([NH2:15])=[NH:14])[CH2:10][CH2:11][OH:12].[C:16](O)(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]>C(Cl)Cl>[C:16]([O:12][CH2:11][CH2:10][N:9]([CH3:8])[C:13]([NH2:15])=[NH:14])(=[O:24])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23]

Participants

6

Reactant 4

HCID 379Octanoic AcidHCID 6367Acetyl chloride2×HCID 83440N-(2-Hydroxyethyl)-N-methylguanidine2×HCID 5284359Calcium Chloride

Product 1

HCID 24985708HCID 24985708, 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 10.66 mL (150 mmol) of acetyl chloride and 25 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 chloride solution is then added slowly with stirring, over a period of 15 minutes, to the Creatinol solution. The solution is stirred for another 10 minutes, after which 13.36 mL (50 mmol) of Octanoic acid is added in one portion and the reaction is slowly heated to about 60° C. for about 4 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 octanoate.

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 60° C. for about 4 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-b4937925b1dd492fa81a0d52c6fd6457
Source dataset
uspto-grants-2009_01
Patent number
US07476749B1

Reaction notes

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