Benzaldehyde → HCID 10086774, compound

Temperature

25 °C

To a solution of 962 mg (4.56 mmol) of the imine derived from benzaldehyde and p-methoxy aniline, and 0.85 mL (6.07 mmol) of triethylamine in 15 mL of CH2Cl2 at -20° C. was added dropwise a solution of 413 mg (3.04 mmol) of α-acetoxy acetyl chloride in 15 mL of CH2Cl2. The reaction mixture was allowed to warm to 25° C. over an 18 h period. The reaction mixture was then diluted with 100 mL of CH2Cl2 and the solution was extracted with 30 mL of 10% aqueous HCl. The organic layer was washed with 30 mL of water and 30 mL of saturated aqueous sodium bicarbonate, dried over sodium sulfate, and concentrated to provide a solid mass. The solid was triturated with 50 mL of hexane and the mixture was filtered. The remaining solid was recrystallized from ethyl acetate/hexane to give 645 mg (68%) of cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one as white crystals, m.p. 163° C.

1. extractionthe solution was extracted with 30 mL of 10% aqueous HCl
2. washThe organic layer was washed with 30 mL of water and 30 mL of saturated aqueous sodium bicarbonate
3. dry with materialdried over sodium sulfate
4. concentrationconcentrated
5. customto provide a solid mass
6. customThe solid was triturated with 50 mL of hexane
7. filtrationthe mixture was filtered
8. customThe remaining solid was recrystallized from ethyl acetate/hexane

ORD record

ord-10e3a3de4a904c68be3a06c12ab2bb06

Source dataset

uspto-grants-1996_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05532363