1,1'-Carbonyldiimidazole → Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamate

HRID 708314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 708314
[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C:9](=[O:10])[C@@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C@H:7]1[CH2:22][NH:23][CH2:24][CH2:25][OH:26].C1N=CN([C:38](N2C=NC=C2)=[O:39])C=1>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:4]=1[CH2:5][N:6]1[C@H:7]([CH2:22][N:23]2[CH2:24][CH2:25][O:26][C:38]2=[O:39])[C@H:8]([NH:11][C:12](=[O:21])[O:13][CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:9]1=[O:10]

Komponenten

4

Edukt 2

HCID 682631,1'-CarbonyldiimidazoleHCID 118411328Benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-(((2-hydroxyethyl)amino)methyl)-4-oxoazetidin-3-yl)carbamate

Produkt 1

HCID 118411331Benzyl((3S,4R)-1-(2,4-dimethoxybenzyl)-2-oxo-4-((2-oxooxazolidin-3-yl)methyl)azetidin-3-yl)carbamateAusbeute 81,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

To a solution of benzyl ((2R,3S)-1-(2,4-dimethoxybenzyl)-2-(((2-hydroxyethyl)amino)methyl)-4-oxoazetidin-3-yl)carbamate (4.47 g, 10.08 mmol) in chloroform (50 ml) was added CDI (4.90 g, 30.2 mmol). After stirring at rt for 30 min it was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 0-5%), affording the title compound (3.84 g, 81%) as a white foam. LCMS: Rt=0.76 min, m/z=470.1 (M+1).

Aufarbeitung

  1. concentrationwas concentrated in vacuo
  2. customThe crude residue was purified via silica gel chromatography (MeOH-DCM, 0-5%)

Quellen und Nachweise

ORD-Eintrag
ord-02d0b21945644ff4b1b9317e2e773f47
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174978B2

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