Palmitic Acid → 2-Methyl-3-pentadecylcarbamoylglycerin

HRID 1380567Notes

Reaction equation

HRID 1380567 reaction equation
C(O)(=O)[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].C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:26])C=CC=CC=1.C([N:38]([CH2:41]C)CC)C.[CH3:43][O:44][CH:45]([CH2:48][OH:49])[CH2:46][OH:47]>C1(C)C=CC=CC=1.ClCCl>[CH3:43][O:44][CH:45]([CH2:48][O:49][C:41](=[O:26])[NH:38][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])[CH2:46][OH:47]

Participants

7

Reactant 4

HCID 985Palmitic AcidHCID 8471TriethylamineHCID 199401P,P-Diphenylphosphinic azideHCID 111709312-Methoxypropane-1,3-diol

Product 1

HCID 543961022-Methyl-3-pentadecylcarbamoylglycerinYield 73%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent2×

Procedure

In 50 ml of toluene is dissolved 5.13 g of n-hexadecanoic acid, and 5.5 g of diphenylphosphorylazide and 3 ml of triethylamine are added. The mixture is stirred for 2 hours and further refluxed for one hour. After cooling, the mixture is dissolved in 20 ml of dichloromethane and the solution is added to 20 ml of dichloromethane containing 4.2 g of 2-methylglycerin is added dropwise over a period of 30 minutes. Then, the mixture is refluxed for 2 hours, followed by addition of 200 ml of ice-water. The mixture is stirred vigorously. The dichloromethane layer is separated, dried over sodium sulfate and concentrated to dryness. The residue is subjected to chromatography on a silica gel (60 g) column [eluent: ethyl acetate-n-hexane (1:1)] to give 5.25 g (yield: 73%) of 2-methyl-3-pentadecylcarbamoylglycerin as a colorless powder.

Workup

  1. additionare added
  2. temperaturefurther refluxed for one hour
  3. temperatureAfter cooling
  4. additionis added dropwise over a period of 30 minutes
  5. temperatureThen, the mixture is refluxed for 2 hours
  6. stirringThe mixture is stirred vigorously
  7. customThe dichloromethane layer is separated
  8. dry with materialdried over sodium sulfate
  9. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-6093b7f75f634822818ce7e95ee61783
Source dataset
uspto-grants-1986_04
Patent number
US04582824

Reaction notes

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