Iodine → HCID 86701040, Verbindung

HRID 1427605Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427605
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.II.[CH2:22]([O:29][N:30]1[C:36](=[O:37])[N:35]2[CH2:38][C@H:31]1[CH2:32][CH2:33][C@H:34]2[C:39]([NH:41][NH:42][C:43](=O)[CH2:44][CH:45]1[CH2:48][CH:47]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[CH2:46]1)=[O:40])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([O:29][N:30]1[C:36](=[O:37])[N:35]2[CH2:38][C@H:31]1[CH2:32][CH2:33][C@H:34]2[C:39]1[O:40][C:43]([CH2:44][CH:45]2[CH2:46][CH:47]([NH:49][C:50](=[O:56])[O:51][C:52]([CH3:55])([CH3:54])[CH3:53])[CH2:48]2)=[N:42][N:41]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Komponenten

5

Edukt 3

HCID 807Iodine2×HCID 11776TriphenylphosphineHCID 86701041HCID 86701041, Verbindung

Produkt 1

HCID 86701040HCID 86701040, VerbindungAusbeute 85,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To s solution of PPh3 (7.9 g, 30.0 mmol) in dry DCM (60 mL) was added I2 (7.8 g, 30.0 mmol). After I2 was dissolved completely, TEA (10.5 mL, 75.0 mmol) was added quickly at rt. The mixture was stirred for 15 mins. Tert-butyl 3-(2-(2-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carbonyl)hydrazinyl)-2-oxoethyl)cyclobutylcarbamate (4.9 g, 15.0 mmol) was added. The mixture was stirred at rt for 1 hr. The solvent was concentrated. EtOAc (300 mL) was added, and the solution was filtered to remove PPh3O. The filtrate was concentrated. The residue was purified by silica gel column chromatography (gradient elution 0-50% EtOAc/petroleum ether) to afford tert-butyl 3-((5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)methyl)cyclobutyl-carbamate (6.2 g, 85%) as a white solid. ESI-MS (EI+, m/z): 484.0 [M+H]+.

Aufarbeitung

  1. stirringThe mixture was stirred at rt for 1 hr
  2. concentrationThe solvent was concentrated
  3. additionEtOAc (300 mL) was added
  4. filtrationthe solution was filtered
  5. customto remove PPh3O
  6. concentrationThe filtrate was concentrated
  7. customThe residue was purified by silica gel column chromatography (gradient elution 0-50% EtOAc/petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-768c9faf69ba45f6a48689685403f6b5
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933232B2

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