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Cesium carbonate → HCID 68312931, Verbindung

HRID 1530439
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1530439
C(OC(N1CCC(C([O:20][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([O-])([O-])=O.[Cs+].[Cs+].[CH2:50]([O:57][C:58](=[O:72])[C:59](Br)([CH3:70])[CH2:60][CH2:61][O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1>CC#N>[CH2:50]([O:57][C:58](=[O:72])[C:59]([O:20][C:21]1[CH:43]=[CH:42][C:24]2[C:25]3[N:29]([CH2:30][CH2:31][O:32][C:23]=2[CH:22]=1)[CH:28]=[C:27]([C:33]1[N:34]([CH:39]([CH3:41])[CH3:40])[N:35]=[C:36]([CH3:38])[N:37]=1)[N:26]=3)([CH3:70])[CH2:60][CH2:61][O:62][CH2:63][C:64]1[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=1)[C:51]1[CH:52]=[CH:53][CH:54]=[CH:55][CH:56]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 68312705HCID 68312705, VerbindungHCID 68312814HCID 68312814, Verbindung

Produkt 1

HCID 68312931HCID 68312931, VerbindungAusbeute 19 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel2×

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 (100 mg, 0.307 mmol) and Cs2CO3 (200 mg, 0.615 mmol) in CH3CN (1 mL) was added a solution of 4-benzyloxy-2-bromo-2-methylbutyric acid benzyl ester (0.345 mmol) in CH3CN (7 mL) and stirring at reflux temperature was continued for 3 h. After cooling to RT, the reaction mixture was partitioned between water and EtOAc. The aqueous phase was extracted with EtOAc and the combined organic layers were washed with water, followed by brine, then dried (Na2SO4) and concentrated in vacuo. The resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% MeOH in DCM) affording 4-Benzyloxy-2-[2-(2-isopropyl-5-methyl-2H-[1,2,4]triazol-3-yl)-4,5-dihydro-6-oxa-1,3a-diazabenzo[e]azulen-8-yloxy]-2-methylbutyric acid benzyl ester as a pale orange gum (36 mg, 19%). LCMS: RT 4.28 min [M+H]+ 622.3

Aufarbeitung

  1. temperatureat reflux temperature
  2. customthe reaction mixture was partitioned between water and EtOAc
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washthe combined organic layers were washed with water
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by column chromatography (Si-PCC, gradient 2-10% MeOH in DCM)

Quellen und Nachweise

ORD-Eintrag
ord-057e103b03c24c898a0a58b7d90497d5
Quelldatensatz
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09090628B2

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