Acetic Acid → methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate

온도

-78 °C

To a solution of methyl 2-[(3R,4R)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (106.9 mg) in tetrahydrofuran (2.1 ml) was added dropwise a solution of n-butyl lithium (0.375 ml of 1.38M solution in hexane) at -78° C. After stirring for 15 minutes at -78° C., the reaction mixture was added with a solution of acetone (0.0385 ml) in tetrahydrofuran (0.3465 ml) at -78° C. After stirring for 25 minutes at -78° C., the reaction mixture was added with acetic acid (0.0493 ml) at -78° C., diluted with ethyl acetate (30 ml), and washed with chilled brine (10 ml), aqueous sodium bicarbonate (10 ml), brine (10 ml), and saturated aqueous sodium chloride (10 ml). After drying over magnesium sulfate, the ethyl acetate extract was filtered and evaporated in vacuo. The residual oil was chromatographed on silica gel (1.2 g) eluting with a mixture of ethyl acetate and hexane (1:5-1:3) to give methyl 2-[(3R,4R)-3-(1-hydroxy-1-methylethyl)-3-isocyano-2-oxo-4-allylazetidin-1-yl]-3-methylbut-2-enoate (96.5 mg) as an oil.

1. stirringAfter stirring for 25 minutes at -78° C.
2. washwashed with chilled brine (10 ml), aqueous sodium bicarbonate (10 ml), brine (10 ml), and saturated aqueous sodium chloride (10 ml)
3. dry with materialAfter drying over magnesium sulfate
4. extractionthe ethyl acetate extract
5. filtrationwas filtered
6. customevaporated in vacuo
7. customThe residual oil was chromatographed on silica gel (1.2 g)
8. washeluting with a mixture of ethyl acetate and hexane (1:5-1:3)

ORD 기록

ord-a93a95eb07ea45f18525d571e7116a75

출처 데이터셋

uspto-grants-1985_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US04539152