Triphenylphosphine → 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one

HRID 577551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 577551
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.[CH2:34]([O:41][C:42]1[C:47]([CH2:48][N:49]([CH2:63][CH2:64][OH:65])[C:50](=[O:62])[C:51]2[C:56](O)=[CH:55][CH:54]=[C:53]([O:58][CH2:59][CH3:60])[C:52]=2[CH3:61])=[C:46]([CH3:66])[CH:45]=[C:44]([CH3:67])[N:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[CH2:34]([O:41][C:42]1[C:47]([CH2:48][N:49]2[C:50](=[O:62])[C:51]3[C:52]([CH3:61])=[C:53]([O:58][CH2:59][CH3:60])[CH:54]=[CH:55][C:56]=3[O:65][CH2:64][CH2:63]2)=[C:46]([CH3:66])[CH:45]=[C:44]([CH3:67])[N:43]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Komponenten

5

Edukt 3

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 86723778N-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-3-ethoxy-6-hydroxy-N-(2-hydroxyethyl)-2-methylbenzamide

Produkt 1

HCID 867237794-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-oneAusbeute 58,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of triphenylphosphine (0.176 g, 0.671 mmol) in THF (5 mL) in an ice bath was treated with diisopropyl azodicarboxylate (0.140 mL, 0.67 mmol) dropwise. After 10 minutes, N-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-3-ethoxy-6-hydroxy-N-(2-hydroxyethyl)-2-methylbenzamide (114e, 0.155 g, 0.334 mmol) was added in one portion. The reaction mixture was stirred in the ice bath overnight and the reaction mixture gradually warmed to room temperature. The reaction mixture was concentrated under vacuum and purified by column chromatography (0-40% ethyl acetate/heptane) to give 4-{[2-(benzyloxy)-4,6-dimethylpyridin-3-yl]methyl}-7-ethoxy-6-methyl-3,4-dihydro-1,4-benzoxazepin-5(2H)-one (114f, 0.087 g, 58%) as a clear, thick oil.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. custompurified by column chromatography (0-40% ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-3eed8709e2dc46d0a6f0fafd6daf9e4a
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09040515B2

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