Ethyl Acetate → HCID 53771611, Verbindung

HRID 903460

Reaktionsgleichung

Reaktionsgleichung von HRID 903460
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([C:6]([CH2:8][CH:9]([CH3:13])[C:10]([OH:12])=O)=[O:7])=[CH:4][CH:3]=1.O[N:17]1[C:21](=O)[CH2:20][CH2:19][C:18]1=O.O1CCOCC1.[C:30]([O-:33])(=[S:32])[CH3:31].[K+].C([O:37][C:38](=[O:40])C)C>C(O)C.O.CCCCCC>[C:30]([S:32][CH:8]([C:6](=[O:7])[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:15][CH:14]=1)[CH:9]([CH3:13])[C:10]([N:17]1[CH2:21][CH2:20][CH2:19][C@H:18]1[C:38]([OH:40])=[O:37])=[O:12])(=[O:33])[CH3:31]

Komponenten

8

Edukt 5

HCID 8857Ethyl AcetateHCID 312751,4-DioxaneHCID 80170N-HydroxysuccinimideHCID 27337154-(4-Chlorophenyl)-2-methyl-4-oxobutanoic acidHCID 23670855Potassium ethanethioate

Produkt 1

HCID 53771611HCID 53771611, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8058HexaneLösungsmittelHCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A solution of 14.3 g. of 3-(4-chlorobenzoyl)-2-methylpropionic acid (Example 47), 7.26 g. of N-hydroxysuccinimide and 13 g. of dicyclohexylcarbidiimide in 150 ml. of dioxane is allowed to stir at room temperature overnight and is then filtered. The filtrate is concentrated at reduced pressure and taken up in 100 ml. of water containing 7.25 g. of L-proline and 10.58 g. of sodium bicarbonate. The mixture is stirred at 25°-35° overnight and filtered through celite. The filtrate is concentrated to remove the ethanol. Concentrated hydrochloric acid is added and the mixture is extracted several times with dichloromethane. The extracts are washed with water and dried (Na2SO4). Evaporation of the solvent yields an amber gum which is dissolved in ethylacetate. Hexane is added, causing white crystals to separate. Recrystallization from ethylacetate gives colorless needles, m.p. 177.5-179.5, labeled isomer A. The preceding compound is brominated as in Example 20 and the product reacted with potassium thioacetate in ethanol-water as in Example 21 to give the product of the Example as a glass.

Aufarbeitung

  1. filtrationis then filtered
  2. concentrationThe filtrate is concentrated at reduced pressure
  3. stirringThe mixture is stirred at 25°-35° overnight
  4. filtrationfiltered through celite
  5. concentrationThe filtrate is concentrated
  6. customto remove the ethanol
  7. additionConcentrated hydrochloric acid is added
  8. extractionthe mixture is extracted several times with dichloromethane
  9. washThe extracts are washed with water
  10. dry with materialdried (Na2SO4)
  11. customEvaporation of the solvent
  12. customyields an amber gum which
  13. customto separate
  14. customRecrystallization from ethylacetate
  15. customgives colorless needles
  16. customto give the product of the Example as a glass

Quellen und Nachweise

ORD-Eintrag
ord-a6af1ed9dcfb483ab06f8046dd2fa84e
Quelldatensatz
uspto-grants-1980_10
Patentnummer
US04226775

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