Oxycinchophen → Talnetant

HRID 651054

Reaktionsgleichung

Reaktionsgleichung von HRID 651054
[OH:1][C:2]1[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12](O)=[O:13])=[CH:9][CH:8]=[CH:7][CH:6]=2.ON1C2C=CC=CC=2N=N1.[CH2:31]([C@H:33]([NH2:40])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.C1COCC1>[CH2:31]([C@H:33]([NH:40][C:12]([C:11]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:2]=1[OH:1])=[O:13])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH3:32]

Komponenten

7

Edukt 4

HCID 10239OxycinchophenHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 6993773(1S)-1-phenylpropan-1-amine

Produkt 1

HCID 5311424TalnetantAusbeute 48,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel2×HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

2.49 g (9.4 mmol) of 3-hydroxy-2-phenylquinoline-4-carboxylic acid (CAS [485-89-2]) were suspended in 150 ml of a 7/3 mixture of THF/CH3CH; 1.40 g (10.3 mmol) of 1-hydroxybenzotriazole (HOBT) and 1.27 g (9.4 mmol) of (S)-α-ethylbenzylamine dissolved in 20 ml of CH2Cl2 were added and the reaction mixture was stirred at room temperature for 30 minutes. 2.13 g (10.3 mmol) of dicyclohexylcarbodiimide (DCC) dissolved in 20 ml of CH2Cl2 were added dropwise. The reaction was left at room temperature overnight, quenched with 20 ml of H2O, evaporated in-vacuo to dryness and dissolved in EtOAc. The precipitated dicyclohexylurea was filtered off and the organic layer was washed with H2O, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl. The organic layer was separated, dried over Na2SO4 and evaporated in-vacuo to dryness; the residue was purified by gradient column chromatography on 60-240 mesh silica gel using a mixture of hexane/EtOAc 9:1 as starting eluent and a mixture of hexane/EtOAc 7:3 as final eluent. The crude product was recrystallized from i-PrOH to yield 1.75 g of the title compound as a white solid.

Aufarbeitung

  1. additionwere added
  2. additionwere added dropwise
  3. waitThe reaction was left at room temperature overnight
  4. customquenched with 20 ml of H2O
  5. customevaporated in-vacuo to dryness
  6. dissolutiondissolved in EtOAc
  7. filtrationThe precipitated dicyclohexylurea was filtered off
  8. washthe organic layer was washed with H2O, 20% citric acid, sat. sol. NaHCO3, sat. sol. NaCl
  9. customThe organic layer was separated
  10. dry with materialdried over Na2SO4
  11. customevaporated in-vacuo to dryness
  12. customthe residue was purified by gradient column chromatography on 60-240 mesh silica gel using
  13. additiona mixture of hexane/EtOAc 9:1
  14. additiona mixture of hexane/EtOAc 7:3 as final eluent
  15. customThe crude product was recrystallized from i-PrOH

Quellen und Nachweise

ORD-Eintrag
ord-0f001969ad0c447b9c251351b1f18450
Quelldatensatz
uspto-grants-2001_08
Patentnummer
US06277862B1

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