2-Azetidinone, 3-(acetyloxy)-4-phenyl-, (3R,4S)- synthesis

6synthesis methods

Product Name:2-Azetidinone, 3-(acetyloxy)-4-phenyl-, (3R,4S)-
CAS Number:144790-01-2
Molecular formula:C11H11NO3
Molecular Weight:205.21

104-94-9 Synthesis

104-94-9
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13831-31-7 Synthesis

13831-31-7
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2-Azetidinone, 3-(acetyloxy)-4-phenyl-, (3R,4S)-

144790-01-2
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186613-02-5 Synthesis

3-(4-METHOXYPHENYL)-2-OXO-4-PHENYLCYCLOBUTYL ACETATE

186613-02-5
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Yield:186613-02-5 645 mg (68%)

Reaction Conditions:

with benzaldehyde;triethylamine in hexane;dichloromethane;

Steps:

1 Preparation of Cis-1-Benzoyl-3-(1-ethoxyethoxy)-4-Phenylazetidinone 2

EXAMPLE 1 Preparation of Cis-1-Benzoyl-3-(1-ethoxyethoxy)-4-Phenylazetidinone 2 cis-1-p-methoxyphenyl-3-acetoxy-4-phenylazetidin-2-one. 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 CH₂ Cl₂ at -20° C. was added dropwise a solution of 413 mg (3.04 mmol) of α-acetoxy acetyl chloride in 15 mL of CH₂ Cl₂. 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 CH₂ Cl₂ 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. cis-3-acetoxy-4-phenylazetidin-2-one.

References:

US5175315,1992,A