Methanol → HCID 131716960, compound

HRID 2247784Notes

Reaction equation

HRID 2247784 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][CH2:12][CH:13]([NH2:17])[C:14]([OH:16])=[O:15])=[O:10])=[CH:3][CH:2]=1.[CH2:18](O)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29].C1(C)C=CC(S(O)(=O)=O)=CC=1.CO>ClCCCl>[CH:1]1[CH:6]=[CH:5][C:4]([CH2:7][O:8][C:9]([CH2:11][CH2:12][C@H:13]([NH2:17])[C:14]([OH:16])=[O:15])=[O:10])=[CH:3][CH:2]=1.[NH2:17][C@H:13]([C:14]([O:16][CH:20]([CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:19][CH3:18])=[O:15])[CH2:12][CH2:11][C:9]([O-:10])=[O:8]

Participants

6

Reactant 4

HCID 887MethanolHCID 6101p-Toluenesulfonic acidHCID 81931-DodecanolHCID 95441Poly-gamma-benzyl L-glutamate

Product 1

HCID 131716960HCID 131716960, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

20 g of poly(γ-benzyl L-glutamate)(molecular weight: 15000; average degree of polymerization: 69) prepared by the NCA method was dissolved in 1,2-dichloroethane. To the resulting solution were added 150 ml of n-dodecyl alcohol and 5 g of p-toluenesulfonic acid. The reaction was allowed to proceed at 60° C. for 15 hours. The reaction mixture was poured into a large amount of methanol to precipitate the formed polymer. The polymer was filtered and dried. Subsequently, the polymer was dissolved in 1,2-dichloroethane again, reprecipitated with methanol, filtered and dried to obtain a purified γ-benzyl L-glutamate/γ-dodecyl L-glutamate copolymer. The ratio of the benzyl ester to the dodecyl ester in the copolymer was determined by NMR and was found to be 61:39.

Workup

  1. customto precipitate the formed polymer
  2. filtrationThe polymer was filtered
  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-a42ecdc9148c47c69c7bcd8d60db85f5
Source dataset
uspto-grants-1991_08
Patent number
US05037186

Reaction notes

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