tert-Butylsulfinamide, (S)-(-)- → tert-butyl 4-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]imidazole-1-carboxylate

HRID 57448

Reaktionsgleichung

Reaktionsgleichung von HRID 57448
[CH:1]([C:3]1[N:4]=[CH:5][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:7]=1)=O.[CH3:15][C:16]([S@@:19]([NH2:21])=[O:20])([CH3:18])[CH3:17]>ClCCCl.[O-]S([O-])(=O)=O.[Cu+2]>[C:16]([S@@:19](/[N:21]=[CH:1]/[C:3]1[N:4]=[CH:5][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH:7]=1)=[O:20])([CH3:18])([CH3:17])[CH3:15]

Komponenten

5

Edukt 2

HCID 11355477tert-Butylsulfinamide, (S)-(-)-HCID 15480636tert-Butyl 4-formyl-1H-imidazole-1-carboxylate

Produkt 1

HCID 90415189tert-butyl 4-[(E)-[(S)-tert-butylsulfinyl]iminomethyl]imidazole-1-carboxylateAusbeute 72,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24462Copper SulfateKatalysatorHCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

To CuSO4 (24.28 g, 152 mmol) and tert-butyl 4-formyl-1H-imidazole-1-carboxylate (19.9 g, 101 mmol) in DCE (100 mL) was added (S)-2-methylpropane-2-sulfinamide (13.52 g, 112 mmol). The reaction was heated to 65° C. for 18 hours. The reaction mixture was then cooled to room temperature and filtered through a pad of celite. The pad was rinsed with DCM (200 mL) and the filtrated was concentrated. The residue was then run through a pad of silica gel with heptane/EtOAc (3:1) as eluent. The filtrate was concentrated to give crude (S,E)-tert-butyl 4-(((tert-butylsulfinyl)imino)methyl)-1H-imidazole-1-carboxylate (22 g). LCMS (B) m/z 300.2 (M+H)+

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationfiltered through a pad of celite
  3. washThe pad was rinsed with DCM (200 mL)
  4. concentrationthe filtrated was concentrated
  5. concentrationThe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-ae39e1d0f11d487da6def10728774fec
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434719B2

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