p-Toluenesulfonic acid → HCID 131716962, compound

HRID 2247785Notes

Reaction equation

HRID 2247785 reaction equation
[NH2:1][C@H:2]([C:8]([O-:10])=[O:9])[CH2:3][CH2:4][C:5]([O-:7])=[O:6].[CH2:11]([OH:17])[CH2:12]CCCC.[C:18]1(C)[CH:23]=[CH:22][C:21](S(O)(=O)=[O:25])=[CH:20][CH:19]=1>CO>[CH3:12][C:11]([O:17][CH2:4][CH2:3][C@H:2]([NH2:1])[C:8]([OH:10])=[O:9])=[O:25].[NH2:1][C@H:2]([C:8]([O:10][CH:18]([CH2:19][CH2:20][CH3:21])[CH2:23][CH3:22])=[O:9])[CH2:3][CH2:4][C:5]([O-:7])=[O:6]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 81031-HexanolHCID 5460544L-glutamate(2-)

Product 1

HCID 131716962HCID 131716962, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

20 g of poly(γmethyl L-glutamate)(molecular weight: 150000; average degree of polymerization: 1050) was dissolved in 300 ml of a 1,2-dichloroethane/tetrachloroethylene(8/2) mixed solvent. To the resulting solution were added 100 ml of n-hexanol and 5 g of p-toluenesulfonic acid. The reaction was allowed to proceed at 60° C. for 20 hr. The reaction mixture was poured into a large amount of methanol to precipitate the formed polymer. The polymer was collected and dried. Subsequently, the polymer was dissolved in 1,2-dichloroethane again, reprecipitated with methanol, filtered and dried to obtain a purified γ-methyl L-glutamate/γ-hexyl L-glutamate copolymer. The ratio of the methyl ester to the hexyl ester in the copolymer was determined by NMR and was found to be 51:49.

Workup

  1. customto precipitate the formed polymer
  2. customThe polymer was collected
  3. customdried
  4. dissolutionSubsequently, the polymer was dissolved in 1,2-dichloroethane again
  5. customreprecipitated with methanol
  6. filtrationfiltered
  7. customdried

Sources & evidence

ORD record
ord-d45a1dc94b6d48e0a4a7dff7b2fdd3dc
Source dataset
uspto-grants-1991_08
Patent number
US05037186

Reaction notes

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