Decanoic Acid → HCID 24985704, compound

HRID 1454015Notes

Reaction equation

HRID 1454015 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:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>C(Cl)Cl>[C:16]([O:12][CH2:11][CH2:10][N:9]([CH3:8])[C:13]([NH2:15])=[NH:14])(=[O:26])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 4

HCID 2969Decanoic AcidHCID 10482Acetyl bromide2×HCID 83440N-(2-Hydroxyethyl)-N-methylguanidine2×HCID 5284359Calcium Chloride

Product 1

HCID 24985704HCID 24985704, 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 10.60 mL (125 mmol) of acetyl bromide 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 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 9.64 mL (50 mmol) of Decanoic acid is added in one portion and the reaction is slowly heated to about 65° C. for about 6 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; 1/5) to yield pure 2-(1-methylguanidino)ethyl decanoate.

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 6 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; 1/5)

Sources & evidence

ORD record
ord-e1e3e7cd884a40c5bb724d9273961d38
Source dataset
uspto-grants-2009_01
Patent number
US07476749B1

Reaction notes

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