4-(PHENYLSULFANYL)AZETIDIN-2-ONE synthesis

6synthesis methods

Product Name:4-(PHENYLSULFANYL)AZETIDIN-2-ONE
CAS Number:31898-69-8
Molecular formula:C9H9NOS
Molecular Weight:179.24

28562-53-0 Synthesis

28562-53-0
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Yield:31898-69-8 62%

Reaction Conditions:

with sodium hydrogencarbonate in water;acetone at 20; for 12 h;

Steps:

4.3.17. General procedure for synthesis of β-lactams containing aromatic thiols, phenol and thiophene

General procedure: Lactams 22 and 24, as well as 26-28 were prepared in a manner similar to the synthesis of lactam 9. 4-Acetoxy-2-azetidone (1 g, 8 mmol) was stirred in 50 mL acetone/water (3:2) and 1.05 equiv of the corresponding substituents (4-mercaptophenol, 4-aminothiophenol, 1,4-benzenedithiol, thiophenol, or 2-thiophene thiol, respectively) was added. Sodium bicarbonate (4 equiv) was added to the mixture, which was then stirred vigorously for 12 h in a closed round bottom flask. Sodium chloride was subsequently added to the solution and after the formation of two layers, the mixture was filtered out and extracted with AcOEt (3 × 50 mL). The combined organic layers were dried over MgSO₄ and concentrated under vacuum. The crude material was purified by flash chromatography or crystallized to give white crystals for all five products in good yield (30-66%).

References:

Kostova, Maya B.;Myers, Carey J.;Beck, Tim N.;Plotkin, Balbina J.;Green, Jacalyn M.;Boshoff, Helena I.M.;Barry III, Clifton E.;Deschamps, Jeffrey R.;Konaklieva, Monika I. [Bioorganic and Medicinal Chemistry,2011,vol. 19,# 22,p. 6842 - 6852] Location in patent:experimental part