Carbon Dioxide → HCID 140522019, compound

HRID 1788326Notes

Reaction equation

HRID 1788326 reaction equation
[C:1](Br)(=[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].[O:19]=[C:20]([CH2:22][N:23]([C:25](=[NH:27])[NH2:26])[CH3:24])[OH:21].N1C=CC=CC=1.C(=O)=O>ClCCl.CC(C)=O>[CH3:24][N:23]([CH2:22][C:20]([OH:21])=[O:19])[C:25]([NH:27][C:1](=[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])=[NH:26]

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 586CreatineHCID 1049PyridineHCID 10041615Hexadecanoyl Bromide4×

Product 1

HCID 140522019HCID 140522019, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

In a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer, a thermometer, a nitrogen inlet tube and the dropping funnel containing the palmitoyl bromide solution, 10.99 g (60 mmol) of creatine is suspended, with stirring, in 100 ml of dry dichloromethane. To this suspension a catalytic amount (0.1 mmol) of pyridine is also added. The suspension is stirred in a dry ice and acetone bath to a temperature of between to about −10° C. and 0° C. When the target temperature is reached the drop wise addition of palmitoyl bromide is commenced. Addition of palmitoyl bromide continues, with cooling and stirring, until all of the palmitoyl bromide is added, after which the reaction is allowed to warm to room temperature with constant stirring. The solution is then filtered to remove any remaining creatine and the volatile dichloromethane and pyridine are removed under reduced pressure yielding 2-(1-methyl-3-palmitoylguanidino)acetic acid.

Workup

  1. customIn a dry 3-necked, round bottomed flask, equipped with a magnetic stirrer
  2. temperaturewith cooling
  3. filtrationThe solution is then filtered
  4. customto remove any remaining creatine
  5. customthe volatile dichloromethane and pyridine are removed under reduced pressure

Sources & evidence

ORD record
ord-c7baff985f1c4b459347dff42e8198b7
Source dataset
uspto-grants-2009_03
Patent number
US07511163B2

Reaction notes

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