Hexanoic Acid → HCID 131731981, compound

HRID 540983Notes

Reaction equation

HRID 540983 reaction equation
[CH2:1]([OH:6])[CH:2]([OH:5])[CH2:3][OH:4].[CH2:7]([OH:12])[CH:8]([OH:11])[CH2:9][OH:10].[CH2:13]([OH:18])[CH:14]([OH:17])[CH2:15][OH:16].[CH2:19]([OH:24])[CH:20]([OH:23])[CH2:21][OH:22].[C:25]([OH:32])(=[O:31])[CH2:26][CH2:27][CH2:28][CH2:29][CH3:30].ON1[C:38](=O)[CH2:37][CH2:36][C:35]1=O.CC(N=C=NC(C)C)C>CS(C)=O>[CH2:27]([CH:26]([CH2:35][CH2:36][CH2:37][CH3:38])[C:25]([OH:32])=[O:31])[CH2:28][CH2:29][CH2:30][CH2:1][CH3:2].[OH:12][CH2:7][CH:8]([CH2:9][OH:10])[OH:11].[OH:18][CH2:13][CH:14]([CH2:15][OH:16])[OH:17].[OH:24][CH2:19][CH:20]([CH2:21][OH:22])[OH:23].[OH:6][CH2:1][CH:2]([CH2:3][OH:4])[OH:5]

Participants

6

Reactant 4

HCID 8892Hexanoic AcidHCID 12734DiisopropylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 1970823756491-53-3

Product 1

HCID 131731981HCID 131731981, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

Into a 250 mL vessel, tetraglycerol (5.0 g, 15.91 mmol) was added and dissolved into anhydrous DMSO (50 mL). Hexanoic acid (11.96 mL, 95.44 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 (0.194 g, 1.59 mmol) and N-hydroxysuccinimide (0.183 g, 1.59 mmol) were both dissolved in the solution. When the catalysts were fully dissolved, N,N-diisopropylcarbodiimide (15.0 mL, 97.03 mmol) was pipetted into the vessel and was sealed to keep the reaction dry. The reaction proceeded overnight at 55° C. The solution was dialyzed in SpectraPor7 MWCO 1000 dialysis tubing to remove the DMSO and unreacted monomer. The polymer crashed out in water into a thick white liquid. After 3 days of dialysis, the solution was placed into a separatory funnel and the organic portion was dissolved into chloroform. The water layer was removed and the organic layer was dried with sodium sulfate. The solvent was stripped via rotoevaporation to leave a clear thick liquid product. NMR analysis supported full conversion of hydroxyl groups to the hexanoic 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. customThe solution was dialyzed in SpectraPor7 MWCO 1000 dialysis
  8. customto remove the DMSO and unreacted monomer
  9. customAfter 3 days of dialysis
  10. customthe solution was placed into a separatory funnel
  11. dissolutionthe organic portion was dissolved into chloroform
  12. customThe water layer was removed
  13. dry with materialthe organic layer was dried with sodium sulfate
  14. customto leave a clear thick liquid product

Sources & evidence

ORD record
ord-43bfbed675ff4b2d8d4de964451f4c84
Source dataset
uspto-grants-2014_10
Patent number
US08871819B2

Reaction notes

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