Ethylene Glycol → HCID 10779799, compound

HRID 378570Notes

Reaction equation

HRID 378570 reaction equation
[C:1]1([C@H:7]([NH:9][C:10]([C:12]2([C:16](=[O:18])[CH3:17])[CH2:15][CH2:14][CH2:13]2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:19](O)[CH2:20][OH:21].C1(C)C=CC(S(O)(=O)=O)=CC=1.C1C=CC=CC=1>O>[C:1]1([C@H:7]([NH:9][C:10]([C:12]2([C:16]3([O:21][CH2:20][CH2:19][O:18]3)[CH3:17])[CH2:15][CH2:14][CH2:13]2)=[O:11])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 241BenzeneHCID 6101p-Toluenesulfonic acidHCID 10490598HCID 10490598, compound

Product 1

HCID 10779799HCID 10779799, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 13.9 g of N-[1-(R)-phenylethyl]-1-acetyl-1-cyclobutanecarboxamide, 15 ml of ethylene glycol, a catalytic amount of p-toluenesulfonic acid and 100 ml of benzene was heated under reflux for 3 hrs. The water formed in the reaction was removed using a Dean-Stark apparatus. After cooling, the mixture was washed with a saturated sodium bicarbonate aqueous solution, then washed with water and then dried. The solvent was removed under reduced pressure to yield 16.5 g of the titled compound as a colorless oil.

Workup

  1. temperatureunder reflux for 3 hrs
  2. customwas removed
  3. temperatureAfter cooling
  4. washthe mixture was washed with a saturated sodium bicarbonate aqueous solution
  5. washwashed with water
  6. customdried
  7. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-64c1164295bf4e57a2e413cd8c98dc86
Source dataset
uspto-grants-2000_02
Patent number
US06031102

Reaction notes

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