(S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one → 4-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzaldehyde

HRID 1850126Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1850126
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([C@@H:9]([NH:11][C:12]2[N:17]=[C:16]([N:18]3[C@@H:22]([CH:23]([CH3:25])[CH3:24])[CH2:21][O:20][C:19]3=[O:26])[CH:15]=[CH:14][N:13]=2)[CH3:10])=[CH:5][CH:4]=1>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH:23]([C@H:22]1[CH2:21][O:20][C:19](=[O:26])[N:18]1[C:16]1[CH:15]=[CH:14][N:13]=[C:12]([NH:11][C@H:9]([C:6]2[CH:5]=[CH:4][C:3]([CH:2]=[O:1])=[CH:8][CH:7]=2)[CH3:10])[N:17]=1)([CH3:24])[CH3:25]

Komponenten

4

Edukt 1

HCID 86730160(S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one

Produkt 1

HCID 867301594-((S)-1-(4-((S)-4-isopropyl-2-oxooxazolidin-3-yl)pyrimidin-2-ylamino)ethyl)benzaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418406HCID 178418406, VerbindungKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of (S)-3-(2-((S)-1-(4-(hydroxymethyl)phenyl)ethylamino)pyrimidin-4-yl)-4-isopropyloxazolidin-2-one (285 mg, 0.8 mmol) and manganese dioxide (2.78 g, 32 mmol, 40 equiv) in DCM (16 mL) was stirred at room temperature for 30 min. The solution was filtered through a pad of celite and washed with DCM. The filtrated was concentrated and used to next step without further purification.

Aufarbeitung

  1. filtrationThe solution was filtered through a pad of celite
  2. washwashed with DCM
  3. concentrationThe filtrated was concentrated
  4. customused to next step without further purification

Quellen und Nachweise

ORD-Eintrag
ord-37fe43ff9140445886004e346fe7ccab
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08957068B2

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