Ethylene Glycol → HCID 15228357, compound

HRID 1608519Notes

Reaction equation

HRID 1608519 reaction equation
[CH:1]([CH:3]([NH:8][C:9](=[O:19])[C@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:11][C:12](=[O:14])[CH3:13])[CH2:4][CH2:5][CH2:6][CH3:7])=[O:2].[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[O:2]1[CH2:20][CH2:21][O:22][CH:1]1[CH:3]([NH:8][C:9](=[O:19])[C@H:10]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:11][C:12](=[O:14])[CH3:13])[CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 15228355HCID 15228355, compound

Product 1

HCID 15228357HCID 15228357, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

In 20 ml of benzene was dissolved 750 mg of N-acetyl-L-leucine-(1-formyl)pentylamide obtained in the same manner as in Example 16-(c), and 1.8 ml of ethylene glycol and a catalytic amount of p-toluenesulfonic acid were added thereto. The mixture was heated at reflux for 3.5 hours. After completion of the reaction, the solvent was removed by distillation under reduced pressure, and the residue was purified by medium-pressure column chromatography on silica gel to obtain 650 mg of the titled compound as a colorless crystal.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 3.5 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by distillation under reduced pressure
  5. customthe residue was purified by medium-pressure column chromatography on silica gel

Sources & evidence

ORD record
ord-f5643b18a0f84c128f9fd5bc25007355
Source dataset
uspto-grants-1995_03
Patent number
US05395824

Reaction notes

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