Oxalic Acid → HCID 57110945, Verbindung

HRID 1464724

Reaktionsgleichung

FC(F)(F)S([O-])(=O)=O.[Sn+2].FC(F)(F)S([O-])(=O)=O.[C:18]([S:22][CH3:23])(=[S:21])[CH2:19][CH3:20].C(O[C@H:28]1[NH:31][C:30](=[O:32])[C@@H:29]1[C@H:33]([O:35][Si:36]([C:39]([CH3:42])([CH3:41])[CH3:40])([CH3:38])[CH3:37])[CH3:34])(=O)C.C(O)(=O)C(O)=O>ClCCl.C(N(CC)CC)C>[C:39]([Si:36]([CH3:37])([CH3:38])[O:35][C@@H:33]([C@@H:29]1[C@@H:28]([S:21][C:18]([S:22][CH3:23])=[CH:19][CH3:20])[NH:31][C:30]1=[O:32])[CH3:34])([CH3:40])([CH3:41])[CH3:42]

Komponenten

Reaktionsbedingungen

Temperatur: -25 °C

Versuchsvorschrift

To a suspension of Tin(II) trifluoromethanesulfonate (5.58 g) in dichloromethane (27 ml) cooled to -25° C. were added triethylamine (1.62 g) and methyl dithiopropionate (1.20 g) successively. The mixture was stirred for 2 hours at -20° C. and (3R,4R)-4-acetoxy-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-2-oxoazetidine (2.0 g) was added thereto. After stirring for 2 hours at 0° C., the mixture was poured into 20% aqueous solution of oxalic acid (100 ml) and the precipitates were filtered off. The organic layer of the filtrate was separated, dried, and concentrated under reduced pressure. The residue was purified by silica gel (50 g) column chromatography (20% ethyl acetate-hexane) to afford (3S,4R)-3-[(1R)-1-(tertbutyldimethylsilyloxy)ethyl]-4-[(1-methylthio-1-propenyl)thio]-2-oxoazetidine (mixture of E and Z isomers) (1.14 g).

Aufarbeitung

stirringAfter stirring for 2 hours at 0° C.
filtrationthe precipitates were filtered off
customThe organic layer of the filtrate was separated
customdried
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel (50 g) column chromatography (20% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag: ord-18770e975bdd4ca0bab87590ee064ff8
Quelldatensatz: uspto-grants-1994_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US05306816

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