Dimethyl Sulfoxide → tert-Butyl [(2S)-2-(3,4-dichlorophenyl)-4-oxobutyl]methylcarbamate

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Reaktionsgleichung

C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:11]([O:15][C:16](=[O:32])[N:17]([CH2:19][C@H:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[CH2:21][CH2:22][OH:23])[CH3:18])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>ClCCl>[C:11]([O:15][C:16](=[O:32])[N:17]([CH2:19][C@H:20]([C:24]1[CH:29]=[CH:28][C:27]([Cl:30])=[C:26]([Cl:31])[CH:25]=1)[CH2:21][CH:22]=[O:23])[CH3:18])([CH3:14])([CH3:12])[CH3:13]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of oxalyl chloride (2.84 mL) in dichloromethane (70 mL) at −78° C. was added dimethylsulfoxide (4.6 mL) in dichloromethane (35 mL). This mixture was stirred for about 7 minutes at −78° C. before (S)-[2-(3,4-dichloro-phenyl)-4-hydroxy-butyl]-methyl-carbamic acid tert-butyl ester (9.1 g) was added as a solution in dichloromethane (25 mL). This mixture was stirred at −78° C. for 30 minutes before triethylamine (18.1 mL) was added neat. The mixture was then stirred for 30 minutes at −78° C., 45 minutes at 0° C., then warmed to ambient temperature. The solution was diluted with dichloromethane, washed with dilute hydrochloric acid, aqueous sodium bicarbonate, dried and evaporated. MS: m/z=346(M+1). The product was used with no further purification.

Aufarbeitung

additionwas added neat
temperaturewarmed to ambient temperature
washwashed with dilute hydrochloric acid, aqueous sodium bicarbonate
customdried
customevaporated
customThe product was used with no further purification

Quellen und Nachweise

ORD-Eintrag: ord-1a365d74ee794d77a0b9f307a5a5f645
Quelldatensatz: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07368461B2

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