Potassium hydroxy sulfite → HCID 53941948, compound

Participants

Reaction Steps

A solution of 4(R)-(phenylsulfanylmethyl)azetidin-2-one (from example 6, step A) (105 mg, 0.543 mmol) in MeOH (3 mL) was treated with an aqueous solution of oxone (167 mg, 0.272 mmol, 3 mL). After stirring at room temperature for 24 h, the reaction mixture was quenched with aqueous Na2S2O3 (10%, 1 mL) and concentrated. The concentrate was diluted with EtOAc (5 mL) and brine (5 mL) and the two layers separated. The aqueous layer was re-extracted three times with CHCl3 (20 mL) and the combined organic phases were dried (MgSO4), filtered and concentrated. The residue was purified by flash chromatography (SiO2, EtOAc) to afford 4(R)-(benzenesulfinylmethyl)azetidin-2-one (89.6 mg, 79% yield). 1H NMR (400 MHz, CDCl3) δ (1:1 mixture of diastereoisomers) 7.61-7.45 (m, 10H), 6.29-6.14 (bs, 1H), 5.70-5.58 (bs, 1H), 4.16-4.08 (m, 1H), 3.88-3.80 (m, 1H), 3.27-3.05 (m, 4H), 2.92 (dd, J=13.3, 9.2 Hz, 1H), 2.90 (dd, J=13.3, 3.5 Hz, 1H), 2.75-2.67 (m, 1H), 2.66-2.58 (m, 1H).

Provenance & Evidence