Triphenylphosphine → 2-{2-[6-Nitro-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl ester

HRID 1858064Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1858064
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][OH:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.[Cl:53][C:54]1[CH:63]=[C:62]2[C:57]([C:58](O)=[C:59]([C:65]3[CH:70]=[C:69]([CH3:71])[CH:68]=[C:67]([CH3:72])[CH:66]=3)[C:60](=[O:64])[NH:61]2)=[CH:56][C:55]=1[N+:74]([O-:76])=[O:75]>>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH2:14][CH2:13][CH:12]1[CH2:17][CH2:18][O:19][C:58]1[C:57]2[C:62](=[CH:63][C:54]([Cl:53])=[C:55]([N+:74]([O-:76])=[O:75])[CH:56]=2)[NH:61][C:60](=[O:64])[C:59]=1[C:65]1[CH:66]=[C:67]([CH3:72])[CH:68]=[C:69]([CH3:71])[CH:70]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 45358666Benzyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 547112387-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one

Produkt 1

HCID 544370152-{2-[6-Nitro-7-chloro-3-(3,5-dimethylphenyl)-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid benzyl esterAusbeute 64 %

Versuchsvorschrift

To a solution of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one (13.5 g in 600 mL of N,N-dimethylformamide) was added 9.2 g of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid benzyl ester and 14 g of triphenylphosphine followed by 10.4 mL of diisopropyl azodicarboxylate and the mixture stirred at room temperature. After 24 hours, the solvents were removed in vacuo and the residue resolvated in methylene chloride, washed with water and purified by flash chromatography on silica gel (hexane:ethyl acetate, 90:10; then methylene chloride:ethyl acetate, 95:5) to give the title compound (13.2 g).

Aufarbeitung

  1. customthe solvents were removed in vacuo
  2. washwashed with water
  3. custompurified by flash chromatography on silica gel (hexane

Quellen und Nachweise

ORD-Eintrag
ord-e5ac50d7bd0b4e8a863f3d0795e26cb7
Quelldatensatz
uspto-grants-2000_11
Patentnummer
US06150352

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