Isopropanol → 2-[(2R, 3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid

HRID 235758ノート

反応式

HRID 235758 の反応式
[OH:1][CH2:2][CH2:3][C@H:4]1[NH:7][C:6](=[O:8])[C@H:5]1[C:9]([O:12][CH3:13])([CH3:11])[CH3:10].CC(C)=[O:16].OS(O)(=O)=O.O=[Cr](=O)=O.C(O)(C)C>CC(C)=O>[CH3:13][O:12][C:9]([C@@H:5]1[C:6](=[O:8])[NH:7][C@@H:4]1[CH2:3][C:2]([OH:16])=[O:1])([CH3:11])[CH3:10]

参加物

5

反応物 3

HCID 3776IsopropanolHCID 56614971(3R, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-oneHCID 131709961Jones' reagent

生成物 1

HCID 536502292-[(2R, 3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid

試薬・触媒・溶媒 1

HCID 180Acetone溶媒2 回

実験手順

A solution of (3R, 4R)-4-(2-hydroxyethyl)-3-(1-methoxy-1-methylethyl)azetidin-2-one (250 mg) in acetone (26.7 ml) as added to a solution of 2N Jones reagent (2.67 ml) in acetone (24.03 ml) at ambient temperature over a period of 40 minutes and the mixture was stirred for another 40 minutes. After addition of an excess of isopropyl alcohol to the mixture, the solvent was distilled off. The residue was dissolved in chloroform and washed with a saturated aqueous sodium chloride. The aqueous layer was extracted four times with chloroform. The extracts were combined, dried over magnesium sulfate, filtered and evaporated. The crystalline residue was washed with hexane to give 2-[(2R, 3R)-3-(1-methoxy-1-methylethyl)-4-oxoazetidin-2-yl]acetic acid (211 mg).

後処理

  1. distillationthe solvent was distilled off
  2. dissolutionThe residue was dissolved in chloroform
  3. washwashed with a saturated aqueous sodium chloride
  4. extractionThe aqueous layer was extracted four times with chloroform
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. washThe crystalline residue was washed with hexane

出典と根拠

ORDレコード
ord-11de8cbcdb48464d867aa4f4d3a14650
出典データセット
uspto-grants-1987_02
特許番号
US04640915

反応ノート

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