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Lithium Hydroxide → Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

HRID 484436
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 484436
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][C:18]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19])[C:5](=C=O)[C@H:6](OC)[NH:7]2.[OH-:27].[Li+].[O:29]1[CH2:33]CCC1>O>[C:33]([C@H:6]1[CH2:5][C@H:4]([NH:17][C:18]([CH2:20][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)=[O:19])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:29])=[O:27]
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Komponenten

5

Edukt 3

HCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86747046trans-5,7-Dichloro-2-methoxy-carbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

Produkt 1

HCID 15168526Trans-2-carboxy-5,7-dichloro-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962Water
Lösungsmittel

Versuchsvorschrift

To a suspension of trans-5,7-dichloro-2-methoxy-carbonyl-4-phenylmethylcarbonylamino-1,2,3,4-tetrahydroquinoline (3.11 g, 7.89 mmol) in a mixture of tetrahydrofuran (100 ml) and water (50 ml) was added aqueous lithium hydroxide (17.4 ml of a 0.5M solution, 8.70 mmol) and the resulting mixture was stirred at room temperture for 3 h. The organic solvent was removed in vacuo and the aqueous residue was acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×100 ml). The combined extracts were washed with saturated brine (1×100 ml), dried (MgSO4) and evaporated to give the crude product which was recrystallised from ethyl acetate/petroleum ether 60-80 to give the title compound as colourless crystals (2 crops, 2.65 g) identical in physical properties to example 34 step b.

Aufarbeitung

  1. customThe organic solvent was removed in vacuo
  2. extractionextracted with ethyl acetate (2×100 ml)
  3. washThe combined extracts were washed with saturated brine (1×100 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customto give the crude product which
  7. customwas recrystallised from ethyl acetate/petroleum ether 60-80

Quellen und Nachweise

ORD-Eintrag
ord-e988fd1a59784dc194f8c048ca209ffd
Quelldatensatz
uspto-grants-1993_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05231102

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