Ethyl Acetate → 5-[(R)-2-{Benzyl-[2-(4-nitrophenyl)ethyl]amino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one

HRID 1039852Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1039852
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11]OS(C2C=CC([N+]([O-])=O)=CC=2)(=O)=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:25]([NH:32][CH2:33][C@@H:34]([C:43]1[CH:52]=[CH:51][C:50]([O:53][CH2:54][C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)=[C:49]2[C:44]=1[CH:45]=[CH:46][C:47](=[O:61])[NH:48]2)[O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C(N(CC)C(C)C)(C)C.CCOC(C)=O>C(#N)C>[CH2:25]([N:32]([CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=1)[CH2:33][C@@H:34]([C:43]1[CH:52]=[CH:51][C:50]([O:53][CH2:54][C:55]2[CH:56]=[CH:57][CH:58]=[CH:59][CH:60]=2)=[C:49]2[C:44]=1[CH:45]=[CH:46][C:47](=[O:61])[NH:48]2)[O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 666727545-[(R)-2-benzylamino 1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-oneHCID 858188714-Nitrobenzenesulfonic Acid 2-(4-Nitrophenyl)ethyl Ester

Produkt 1

HCID 667718165-[(R)-2-{Benzyl-[2-(4-nitrophenyl)ethyl]amino}-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-oneAusbeute 50,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A stirred solution of 4-nitrobenzenesulfonic acid 2-(4-nitrophenyl)ethyl ester (3.78 g, 10.7 mmol); 5-[(R)-2-benzylamino-1-(tert-butyldimethylsilanyloxy)ethyl]-8-benzyloxy-1H-quinolin-2-one (4.620 g, 8.975 mmol) and N,N-diisopropylethylamine (3.59 mL, 20.6 mmol) in acetonitrile (39.2 mL) was heated at 65° C. overnight. After cooling the reaction mixture to room temperature, EtOAc (20 mL) was added and this mixture was washed with brine (20 mL). The organic layer was dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-30% EtOAc in hexanes) to give the title compound (3.0 g, 50% yield) as a yellow oil.

Aufarbeitung

  1. washthis mixture was washed with brine (20 mL)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (0-30% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-db115fa9410a457d85f485d5d43ef36f
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08551978B2

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