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Triphenylphosphine → HCID 68313148, Verbindung

HRID 1530385
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530385
C(OC(N1CCC(C(O[C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)CC)CC1)=O)C1C=CC=CC=1.[C:44]([O:48][C:49]([N:51]1[CH2:57][CH2:56][CH2:55][CH:54]([CH:58]([OH:60])[CH3:59])[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:46])[CH3:45].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>O1CCOCC1.CCOC(C)=O>[C:44]([O:48][C:49]([N:51]1[CH2:57][CH2:56][CH2:55][CH:54]([CH:58]([O:60][C:21]2[CH:43]=[CH:42][C:24]3[C:25]4[N:29]([CH2:30][CH2:31][O:32][C:23]=3[CH:22]=2)[CH:28]=[C:27]([C:33]2[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=2)[N:26]=4)[CH3:59])[CH2:53][CH2:52]1)=[O:50])([CH3:47])([CH3:46])[CH3:45]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 68312705HCID 68312705, VerbindungHCID 68312905HCID 68312905, Verbindung

Produkt 1

HCID 68313148HCID 68313148, VerbindungAusbeute 15 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8857
Ethyl Acetate
Lösungsmittel
HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a suspension of 2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-ol from Example 4 (267 mg, 0.82 mmol), 4-(1-hydroxyethyl)azepane-1-carboxylic acid tertbutyl ester (300 mg, 1.23 mmol) and triphenylphosphine (365 mg, 1.39 mmol) in dioxane (3 mL) was added dropwise DIAD (273 ul, 1.39 mmol) and the reaction mixture was stirred at RT for 2 h. The mixture was then diluted with EtOAc and washed with aq. NaOH (1N). The aqueous phase was extracted with EtOAc (×3) and the combined organic layers were then washed with brine, dried over MgSO4 and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM followed by Si-PCC, gradient 0-10% MeOH in EtOAc) affording the title compound as a colorless oil (60 mg, 15%). LCMS: RT 4.08 min [M+H]+ 551.2

Aufarbeitung

  1. washwashed with aq. NaOH (1N)
  2. extractionThe aqueous phase was extracted with EtOAc (×3)
  3. washthe combined organic layers were then washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 0-10% MeOH in DCM followed by Si-PCC, gradient 0-10% MeOH in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-802580a81d6140119489fee8d4fe39c7
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090628B2

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