Dimethyl Sulfoxide → Benzyl N-methyl-N-(2-oxoethyl)carbamate
Reaktionsgleichung
CS(C)=O.CCN(C(C)C)C(C)C.[CH2:14]([O:21][C:22]([N:24]([CH2:26][CH2:27][OH:28])[CH3:25])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[CH2:14]([O:21][C:22]([N:24]([CH2:26][CH:27]=[O:28])[CH3:25])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- -10 °C
Versuchsvorschrift
DMSO (71 mL, 1 mol) and DIPEA (87.1 mL, 0.5 mol) were added to a stirred solution of the product of step (a) (20.9 g, 0.1 mol) in dichloromethane (200 mL) at −10° C. The reaction mixture was stirred at −10° C. for 15 min and then sulfur trioxide pyridine complex (79.6 g, 0.5 mol) was added and the resulting mixture was stirred for 1 hour. The reaction mixture was quenched with addition of 1M hydrochloric acid (200 mL). The organic layer was separated and washed with saturated aqueous sodium bicarbonate (100 mL), brine (100 mL), dried (potassium carbonate) and solvent removed under reduced pressure to give the title compound (20.7 g, ˜100% yield).
Aufarbeitung
- additionsulfur trioxide pyridine complex (79.6 g, 0.5 mol) was added
- stirringthe resulting mixture was stirred for 1 hour
- customThe reaction mixture was quenched with addition of 1M hydrochloric acid (200 mL)
- customThe organic layer was separated
- washwashed with saturated aqueous sodium bicarbonate (100 mL), brine (100 mL)
- dry with materialdried (potassium carbonate) and solvent
- customremoved under reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-fe4eeb479c9240408b7063291feaca0d
- Quelldatensatz
- uspto-grants-2015_03
- Patentnummer
- US08969571B2
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