Hydrogen Peroxide → (2R)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid

HRID 2258287ノート

反応式

HRID 2258287 の反応式
OO.[OH-].[Li+].C([C@@H]1COC(=O)N1[C:18](=[O:38])[C@H:19]([CH2:23][C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[C:26]([O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37])[CH:25]=1)[CH:20]([CH3:22])[CH3:21])C1C=CC=CC=1.S([O-])([O-])=[O:40].[Na+].[Na+].C(=O)([O-])O.[Na+]>O1CCCC1.O>[CH3:31][O:30][C:27]1[CH:28]=[CH:29][C:24]([CH2:23][C@H:19]([CH:20]([CH3:21])[CH3:22])[C:18]([OH:38])=[O:40])=[CH:25][C:26]=1[O:32][CH2:33][CH2:34][CH2:35][O:36][CH3:37]

参加物

7

反応物 5

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 24437Sodium SulfiteHCID 516892Sodium BicarbonateHCID 22865790(R)-4-benzyl-3-((R)-2-(4-methoxy-3-(3-methoxypropoxy)benzyl)-3-methylbutanoyl)oxazolidin-2-one

生成物 1

HCID 9944529(2R)-2-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-3-methylbutanoic acid

試薬・触媒・溶媒 1

HCID 21881883Oxolane--water (1/1)溶媒

反応条件

温度
0 °C

実験手順

With ice-cooling, a 30% hydrogen peroxide solution (434 ml) and lithium hydroxide 98% (31.2 g) are added to a solution of 4(R)-benzyl-3-{2(R)-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methyl-butyryl}-oxazolidin-2-one (300 g) in tetrahydrofuran/water 3:1 (4.8 liters). When the addition is complete, the temperature of the reaction mixture is allowed to rise to room temperature over the course of 3 hours; the batch is then cooled again to 0° C. and a 1.5M aqueous sodium sulfite solution (2.55 liters) and then a saturated aqueous sodium hydrogen carbonate solution (1 liter) are added dropwise over the course of 30 minutes. The mixture is concentrated under reduced pressure and the aqueous solution so obtained is washed with dichloromethane (3×3 liters). The aqueous phase is adjusted to pH 3 by the addition of 2N hydrochloric acid, extracted with dichloromethane (3×3 liters), and the combined organic phases are dried over magnesium sulfate and concentrated. The title compound is obtained in the form of an oil (186.8 g), which can be caused to crystallise in hexane/diethyl ether at -20° C.: m.p. 43.5°-44° C. Rf (ethyl acetate/hexane 2:1)=0.30. Anal. C17H26O5 (310.39): calc. C, 65.78; H, 8.44; found C, 65.96; H, 8.70.

後処理

  1. temperatureWith ice-cooling
  2. additionWhen the addition
  3. customto rise to room temperature over the course of 3 hours
  4. concentrationThe mixture is concentrated under reduced pressure
  5. customthe aqueous solution so obtained
  6. washis washed with dichloromethane (3×3 liters)
  7. additionThe aqueous phase is adjusted to pH 3 by the addition of 2N hydrochloric acid
  8. extractionextracted with dichloromethane (3×3 liters)
  9. dry with materialthe combined organic phases are dried over magnesium sulfate
  10. concentrationconcentrated

出典と根拠

ORDレコード
ord-b5f4f05f81df49a9b28889ae1be44c02
出典データセット
uspto-grants-1997_08
特許番号
US05659065

反応ノート

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