Potassium hydroxy sulfite → HCID 53941948、化合物

HRID 321944ノート

反応式

HRID 321944 の反応式
[C:1]1([S:7][CH2:8][C@@H:9]2[NH:12][C:11](=[O:13])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:14]OS([O-])=O.[K+]>CO>[C:1]1([S:7]([CH2:8][C@@H:9]2[NH:12][C:11](=[O:13])[CH2:10]2)=[O:14])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

4

反応物 2

HCID 23707502Potassium hydroxy sulfiteHCID 53809484HCID 53809484、化合物

生成物 1

HCID 53941948HCID 53941948、化合物収率 157.4%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8d30855aff5f452b96099b2ba8b5a052
出典データセット
uspto-grants-2001_04
特許番号
US06211170B1

反応ノート

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