Dichloromethane → 1-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

HRID 268604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 268604
F[C:2](F)(F)[C:3]([OH:5])=[O:4].O=S1(=O)C[CH2:12][CH:11](N)[CH2:10]1.CC[N:18]([CH:22]([CH3:24])[CH3:23])[CH:19]([CH3:21])[CH3:20].C(O[BH-](O[C:35](=[O:37])C)OC(=O)C)(=O)C.[Na+].Cl[CH2:40]Cl>O>[CH:22]([N:18]1[C:19]2[C:20](=[CH:10][CH:11]=[CH:12][CH:21]=2)[CH:40]=[C:2]([C:3]([OH:5])=[O:4])[C:35]1=[O:37])([CH3:23])[CH3:24]

Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 668595081,1-Dioxotetrahydro-1lambda6-thiophen-3-ylamine trifluoroacetic acid salt

Produkt 1

HCID 109442901-Isopropyl-2-oxo-1,2-dihydro-3-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

1,1-dioxotetrahydro-1λ6-thiophen-3-ylamine trifluoroacetic acid salt (500 mg; 2 mmol), N,N′-diisopropylethylamine (0.35 mL), and sodium triacetoxyborohydride (422 mg; 2 mmol) was added to a vial containing 10 mL of dichloromethane. The mixture was stirred for 5 minutes prior to the addition of 1-isopropyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid {(1S, 3R, 5R)-8-[(2,2-dihydroxy)ethyl]-8-azabicyclo[3.2.1]oct-3-yl}amide (0.427 g). The final mixture was stirred for 1 h, at which time the reaction was judged to be complete based on HPLC and mass spectrometric analysis. Water (20 mL) was slowly added to quench the remaining reducing agent. The mixture was diluted with 100 mL of dichloromethane, and shaken in a funnel before collecting the organic layer. The organic layer was washed with 1M NaOH (40 mL) and brine (50 mL), dried over MgSO4, and evaporated to yield the title intermediate as a colorless solid. This crude product was used in the next step without further treatment.

Aufarbeitung

  1. customto quench the
  2. additionThe mixture was diluted with 100 mL of dichloromethane
  3. stirringshaken in a funnel
  4. custombefore collecting the organic layer
  5. washThe organic layer was washed with 1M NaOH (40 mL) and brine (50 mL)
  6. dry with materialdried over MgSO4
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3c76f639dd3b4d189b0db4c596f9b8f3
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446114B2

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