반응 #215076

반응 방정식

potassium persulfate

sodium monohydrogen phosphate

methyl 3-t-butoxycarbonylamino-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate

→

title compound

수율 31.0%

Methyl cis-3-t-Butoxycarbonylamino-4-oxoazetidine-2-carboxylate

수율 31.0%

용매

water

acetonitrile

반응 조건

후처리

1. 1
   온도warmed to 80°
2. 2
   기타is consumed (tlc)
3. 3
   온도The reaction mixture is cooled
4. 4
   농축concentrated in vacuum
5. 5
   workup.STIRRINGshaken with ethyl acetate-water
6. 6
   세척The organic phase is washed with dilute HCl, NaHCO3 solution and brine
7. 7
   건조dried over magnesium sulfate
8. 8
   기타evaporated to dryness
9. 9
   기타The residue is chromatographed over silica gel with 1:1 benzene-ethyl acetate
10. 10
    기타to afford pure product which
11. 11
    기타crystallized from ethyl acetate-hexane

실험 절차

A solution of 10.5 g (26.7 mmole) of methyl 3-t-butoxycarbonylamino-1-(2,4-dimethoxybenzyl)-4-oxoazetidine-2-carboxylate in 500 ml of acetonitrile is degassed with argon and warmed to 80°. A degassed solution of 15 g (55.5 mmole) of potassium persulfate and 7.5 g (28 mmole) of sodium monohydrogen phosphate in 150 ml of water is added in five portions over 1 hr. The reaction is stirred at 80°-85° under argon for 2-3 hrs until all starting material is consumed (tlc). The reaction mixture is cooled, concentrated in vacuum, shaken with ethyl acetate-water. The organic phase is washed with dilute HCl, NaHCO3 solution and brine; dried over magnesium sulfate and evaporated to dryness. The residue is chromatographed over silica gel with 1:1 benzene-ethyl acetate to afford pure product which crystallized from ethyl acetate-hexane to yield 2.0 g (31%) of the title compound. A less pure fraction from the column, is crystallized from ethyl acetate-hexane to give an additional 0.5 g of product, overall yield, 38%.

출처