Potassium hydroxy sulfite → HCID 53941948, compound

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).

1. customthe reaction mixture was quenched with aqueous Na2S2O3 (10%, 1 mL)
2. concentrationconcentrated
3. additionThe concentrate was diluted with EtOAc (5 mL) and brine (5 mL)
4. customthe two layers separated
5. extractionThe aqueous layer was re-extracted three times with CHCl3 (20 mL)
6. dry with materialthe combined organic phases were dried (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated
9. customThe residue was purified by flash chromatography (SiO2, EtOAc)

ORD record

ord-8d30855aff5f452b96099b2ba8b5a052

Source dataset

uspto-grants-2001_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06211170B1