反応 #343960

反応方程式

4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl) -2-oxo-1-carbapenam-3-carboxylate

trifluoromethanesulfonic anhydride

vinyl(tri-n-butyl)tin

diisopropylethylamine

tri(2-furyl)phosphine

→

title compound

収率 47.9%

4-Nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl)-2-vinyl-1-carbapen-2-em-3-carboxylate

収率 47.9%

溶媒

ethyl acetate

ethyl acetate

N-methylpyrrolidinone

acetonitrile

反応条件

後処理

1. 1
   洗浄the organic layer was washed with saturated aqueous sodium bicarbonate
2. 2
   乾燥After the extract was dried over anhydrous magnesium sulfate
3. 3
   その他the solvent was removed
4. 4
   その他the next reaction
5. 5
   その他without purification
6. 6
   workup.STIRRINGthe mixture was stirred for 2 hours at room temperature
7. 7
   洗浄the organic layer was washed with water
8. 8
   乾燥After the extract was dried over anhydrous magnesium sulfate
9. 9
   その他the solvent was removed
10. 10
    その他The residue was purified by silica gel column chromatography (elution with ethyl acetatehexane system)

実験手順

Under a nitrogen atmosphere, to a solution of 128 mg (0.368 mmol) of 4-nitrobenzyl (5R,6S)-6-((1R)-1-hydroxyethyl) -2-oxo-1-carbapenam-3-carboxylate in acetonitrile (3 ml), followed by 0.065 ml (0.37 mmol) of diisopropylethylamine at -45° C., followed by 0.062 ml (0.37 mmol) of trifluoromethanesulfonic anhydride, and the mixture was stirred for 2 hours at the same temperature. To the reaction mixture was added ethyl acetate (3 ml), and the organic layer was washed with saturated aqueous sodium bicarbonate followed by saturated aqueous sodium chloride. After the extract was dried over anhydrous magnesium sulfate, the solvent was removed. The residual triflate was used the next reaction without purification. To 181 mg of this crude product was added 108 mg (0.79 mmol) of zinc chloride, 5.1 mg (0.0087 mmol) of bis(benzylideneacetone)-palladium(0), and 4.2 mg (0.018 mmol) of tri(2-furyl)phosphine was added a solution of 132 mg (0.416 mmol) of vinyl(tri-n-butyl)tin in N-methylpyrrolidinone (6 ml), and the mixture was stirred for 2 hours at room temperature. To the reaction mixture was added ethyl acetate, and the organic layer was washed with water followed by saturated aqueous sodium chloride. After the extract was dried over anhydrous magnesium sulfate, the solvent was removed. The residue was purified by silica gel column chromatography (elution with ethyl acetatehexane system) to give 60.3 mg (yield: 47.9%) of the title compound.

出典