Chloride → 4-Methoxybenzyl 2-[(3R,4R)-3-Phenylacetamido-4-[(2RS, 3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]-2-tri-n-butylphosphoranylideneacetate

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4-Methoxybenzyl (2RS)-2-hydroxy-2-[(3R,4R)-3-phenylacetamido-4-[(2RS,3SR)-3-methyltetrahydrofuran-2-ylcarbonylmethylthio]azetidin-2-on-1-yl]acetate (10.406 g) was converted to it's chloride with thionyl chloride (3.34 g, 2.02 ml) and 2,6-lutidine (3.009, 3.25 ml) in tetrahydrofuran (100 ml) as described in Example 6(c). The crude chloride in dioxan (80 ml) was then converted to the product with tri-n-butylphosphine (6.98 ml) also described in 6(c). Flash chromatography on silica gel afforded the title compound as a foam (6.525 g, 47%). [Mass spectrum: +ve ion (3-nitrobenzyl alcohol, sodium acetate) MNa+ (763)].

Provenance & Evidence