反应详情

0.14 ml (0.21 mmol) of a cyclohexane solution containing 1.5M of a lithiumdiisopropylamide-tetrahydrofuran complex was added to 2 ml of an ice-cooled tetrahydrofuran suspension containing 91 mg (0.352 mmol) of a magnesium bromide-diethyl ether complex, and the resulting mixture was stirred for 10 minutes an this temperature. At the end of this time, 2 ml of a tetrahydrofuran solution containing 55 mg (0.207 mmol) of 2-(4-nitrobenzyloxycarbonyl)aminoethylmercaptan were added to the mixture, which was then stirred for a further 10 minutes in an ice bath. 102 mg (0.174 mmol) of the S-oxide isomer of lower polarity of the 4-nitrobenzyl (1R,5S,6S)-6-[1(R)-t-butyldimethylsilyloxyethyl]-1-methyl-2-phenylsulfinyl-1-carbapen-2-em-3-carboxylate (prepared as described in Preparation 2) were then added to the mixture, and the mixture was stirred for a further 15 minutes. At the end of this time, a saturated aqueous solution of ammonium chloride was added, and then the mixture was extracted with ethyl acetate. The resulting organic extract was washed first with water and then with a saturated aqueous solution of sodium chloride, after which the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through 15 g of silica gel, using a 1:19 by volume mixture of ethyl acetate and hexane as the eluent, to give 104 mg (yield 84%) of the title compound as a foam-like solid.

1. additioncontaining 91 mg (0.352 mmol) of a magnesium bromide-diethyl ether complex
2. additionwere added to the mixture, which
3. stirringwas then stirred for a further 10 minutes in an ice bath
4. stirringthe mixture was stirred for a further 15 minutes
5. extractionthe mixture was extracted with ethyl acetate
6. extractionThe resulting organic extract
7. washwas washed first with water
8. customwith a saturated aqueous solution of sodium chloride, after which the solvent was removed by distillation under reduced pressure
9. customThe residue was purified by column chromatography through 15 g of silica gel
10. additionby volume mixture of ethyl acetate and hexane as the eluent