Octanoic Acid → HCID 131731982, compound

HRID 540988Notes

Reaction equation

HRID 540988 reaction equation
[CH3:1][CH2:2][C:3]([CH2:8][OH:9])([CH2:6][OH:7])CO.[C:10]([OH:19])(=[O:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].[OH:20]N1C(=O)C[CH2:23][C:22]1=O.[CH3:28][CH:29](N=C=NC(C)C)C>C1COCC1>[CH2:12]([CH:11]([CH2:28][CH2:29][CH2:8][CH2:3][CH2:2][CH3:1])[C:10]([OH:19])=[O:18])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:22][CH3:23].[OH:9][CH2:8][CH:3]([CH2:6][OH:7])[OH:20].[OH:9][CH2:8][CH:3]([CH2:6][OH:7])[OH:18].[OH:9][CH2:8][CH:3]([CH2:6][OH:7])[OH:18].[OH:9][CH2:8][CH:3]([CH2:6][OH:7])[OH:18].[OH:9][CH2:8][CH:3]([CH2:6][OH:7])[OH:18].[OH:9][CH2:8][CH:3]([CH2:6][OH:7])[OH:18]

Participants

6

Reactant 4

HCID 379Octanoic AcidHCID 6510TrimethylolpropaneHCID 12734DiisopropylcarbodiimideHCID 80170N-Hydroxysuccinimide

Product 1

HCID 131731982HCID 131731982, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Into a 250 mL vessel, hexaglycerol (5.0 g, 10.81 mmol) was added and dissolved into anhydrous THF (50 mL). Octanoic acid (13.71 mL, 86.49 mmol) was also dissolved into the reaction mixture which was stirred magnetically at room temperature for one hour to fully dissolve the reagents. N,N-dimethylaminopyridine (0.132 g, 1.08 mmol) and N-hydroxysuccinimide (0.124 g, 1.08 mmol) were both dissolved in the solution. When the catalysts were fully dissolved, N,N-diisopropylcarbodiimide (13.54 mL, 87.57 mmol) was pipetted into the vessel and was sealed to keep the reaction dry. The reaction proceeded overnight at 55° C. The solution was stripped of THF via rotoevaporation and redissolved into chloroform. The organic layer was washed 2× with sodium bicarbonate buffer and 2× with deionized water to remove unreacted starting materials. The chloroform was removed to yield a clear viscous liquid. NMR analysis supported full conversion of hydroxyl groups to the octanoic esters.

Workup

  1. dissolutionto fully dissolve the reagents
  2. dissolutionboth dissolved in the solution
  3. dissolutionWhen the catalysts were fully dissolved
  4. customwas sealed
  5. customdry
  6. waitThe reaction proceeded overnight at 55° C
  7. dissolutionredissolved into chloroform
  8. washThe organic layer was washed 2× with sodium bicarbonate buffer and 2× with deionized water
  9. customto remove unreacted
  10. customThe chloroform was removed
  11. customto yield a clear viscous liquid

Sources & evidence

ORD record
ord-be55b8f1b2fd4e76b54b8d04df74eccc
Source dataset
uspto-grants-2014_10
Patent number
US08871819B2

Reaction notes

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