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Triphenylphosphine → 2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1858073
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1858073
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:27]=[C:26]2[C:21]([C:22](O)=[C:23]([C:29]3[CH:34]=[C:33]([CH3:35])[CH:32]=[C:31]([CH3:36])[CH:30]=3)[C:24](=[O:28])[NH:25]2)=[CH:20][C:19]=1[N+:38]([O-:40])=[O:39].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][O:16][C:22]1[C:21]2[C:26](=[CH:27][C:18]([Cl:17])=[C:19]([N+:38]([O-:40])=[O:39])[CH:20]=2)[NH:25][C:24](=[O:28])[C:23]=1[C:29]1[CH:30]=[C:31]([CH3:36])[CH:32]=[C:33]([CH3:35])[CH:34]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
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Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5103438Tert-butyl 2-(2-hydroxyethyl)piperidine-1-carboxylateHCID 547112387-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro-1H-quinolin-2-one

Produkt 1

HCID 54394346
2-{2-[7-Chloro-3-(3,5-dimethylphenyl)-6-nitro-2-oxo-1,2-dihydroquinolin-4-yloxy]-ethyl}-piperidine-1-carboxylic acid tert-butyl ester
Ausbeute 74,5 %

Versuchsvorschrift

To a solution of 2-(2-hydroxyethyl)-piperidine-1-carboxylic acid tert-butyl ester (0.864 g in 38 mL dry tetrahydrofuran) was added 1.56 g of 7-chloro-3-(3,5-dimethylphenyl)-4-hydroxy-6-nitro- 1H-quinolin-2-one followed by 1.19 g of triphenylphosphine and the mixture stirred at room temperature. To this was added 0.72 mL of diethyl azodicarboxylate (DEAD) and stirring was continued for 64 hours. At this time the solvents were removed in vacuo and the residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 6:4) to give the title compound (1.56 g).

Aufarbeitung

  1. stirringstirring
  2. customAt this time the solvents were removed in vacuo
  3. customthe residue purified by flash chromatography on silica gel (hexane:ethyl acetate, 6:4)

Quellen und Nachweise

ORD-Eintrag
ord-e2108b39771e41d4a5f32cd21f5a2382
Quelldatensatz
uspto-grants-2000_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06150352

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