Triethylamine → HCID 58691133, compound

Participants

Reaction Steps

To m-methoxyacetophenone (7.5 g, 50 mmol) and triethylamine (10.5 ml, 75 mmol) in dichloromethane (200 ml) was dropped at 0° C. under stirring trifluoromethanesulfonic acid trimethylsilyl ester (10.9 ml, 60 mmol) and the mixture was stirred at room temperature for 1 hour. To the reaction mixture was added at room temperature (2R,3R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-oxo-2-azetidinyl acetate (14.4 g, 50 mmol) and zinc iodide (9.6 g, 30 mmol), and the mixture was stirred for 2 hours. To the reaction mixture was added a 5% aqueous potassium hydrogensulfate solution (250 ml), and an organic layer was separated by a separatory funnel. An aqueous layer was extracted with chloroform (100 ml×twice). The extract was combined with the organic layer, dried over magnesium sulfate, filtered and concentrated. The residue was purified with silica gel chromatography (silica gel 400 g, hexane:ethyl acetate=2:1˜0:1) to give (3S,4R)-3-((1R)-1-{[tert-butyl(dimethyl)silyl]oxy}ethyl)-4-[2-(3-methoxyphenyl)-2-oxoethyl]azetidin-2-one (15.91 g, yield 84%) as a pale yellowish solid.

Provenance & Evidence