Ethanol → HCID 22122139, compound

HRID 1859188Notes

Reaction equation

HRID 1859188 reaction equation
[C:1]([C:3]1[CH:31]=[CH:30][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH:17]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:18][C:19]([OH:21])=[O:20])[C:13](=[O:28])[C:12]2=[O:29])=[CH:5][CH:4]=1)#[N:2].S(Cl)(Cl)=O.[CH2:36](O)[CH3:37]>>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][N:14]([CH:17]([C:22]3[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=3)[CH2:18][C:19]([O:21][CH2:36][CH3:37])=[O:20])[C:13](=[O:28])[C:12]2=[O:29])=[CH:30][CH:31]=1)#[N:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 22122128HCID 22122128, compound

Product 1

HCID 22122139HCID 22122139, compound

Procedure

In 14 ml of ethanol was suspended 0.70 g of (-)-3-[4-[3-(4-cyanophenoxy)propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionic acid, followed by adding thereto 0.15 ml of thionyl chloride under ice-cooling, and the resulting mixture was heated under reflux for 1 hour. After completion of the reaction, the solvent was distilled off under reduced pressure and 10 ml of ethyl acetate and 10 ml of water were added to the resulting residue, and the pH was adjusted to 7.5 with a saturated aqueous sodium hydrogencarbonate solution. The organic layer was separated and the aqueous layer was extracted three times with ethyl acetate. The combined organic layer was washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate, after which the solvent was distilled off under reduced pressure to obtain 0.5 g of ethyl (-)-3-[4-[3-(4-cyanophenoxy)propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionate as colorless crystals having a melting point of 110.5-112° C.

Workup

  1. additionby adding
  2. temperaturethe resulting mixture was heated
  3. temperatureunder reflux for 1 hour
  4. customAfter completion of the reaction
  5. distillationthe solvent was distilled off under reduced pressure and 10 ml of ethyl acetate and 10 ml of water
  6. additionwere added to the resulting residue
  7. customThe organic layer was separated
  8. extractionthe aqueous layer was extracted three times with ethyl acetate
  9. washThe combined organic layer was washed with a saturated aqueous sodium chloride solution
  10. dry with materialdried over anhydrous magnesium sulfate
  11. distillationafter which the solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-b0b11cda754943c09ecddb927318b6b1
Source dataset
uspto-grants-2000_11
Patent number
US06153613

Reaction notes

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