Hydrogen Peroxide → (R)-3-cyclopentyl-2-phenyl-propionic acid

HRID 889593ノート

反応式

HRID 889593 の反応式
[OH2:1].[OH-].[Li+].OO.[CH:6]1([CH2:11][C@H:12]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:13](N2[C@H](C)[C@H](C3C=CC=CC=3)OC2=O)=[O:14])[CH2:10][CH2:9][CH2:8][CH2:7]1>C1COCC1>[CH:6]1([CH2:11][C@H:12]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:13]([OH:14])=[O:1])[CH2:7][CH2:8][CH2:9][CH2:10]1

参加物

5

反応物 3

HCID 784Hydrogen PeroxideHCID 168937Lithium hydroxide, monohydrateHCID 67024850(4R,5S)-3-((R)-3-cyclopentyl-2-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one

生成物 1

HCID 44248629(R)-3-cyclopentyl-2-phenyl-propionic acid

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Lithium hydroxide monohydrate (1.28 g, 30.6 mmol) is suspended in THF (50 mL) and cooled to 0° C. Hydrogen peroxide (50 wt % in water, 2.81 mL, 91.79 mmol) is added dropwise. Reaction is stirred at 0° C. for 15 min and the title C compound, (4R,5S)-3-((R)-3-cyclopentyl-2-phenyl-propionyl)-4-methyl-5-phenyl-oxazolidin-2-one (3.85 g, 10.2 mmol) is added in five separate portions, allowing portions to dissolve completely between additions. The reaction is allowed to stir and warm to RT overnight. The reaction is then concentrated to a sticky white solid. This is dissolved in ethyl acetate (25 mL)/1 N HCl (25 mL). The organic solution is dried over anhydrous sodium sulfate, filtered, and concentrated to afford the crude product as a yellow oil. The crude product is chromatographed over silica eluting with 5→65% ethyl acetate in hexanes to afford (R)-3-cyclopentyl-2-phenyl -propionic acid as a white solid: 1H NMR (400 MHz, CDCl3) δ 1.1 (m, J=11.6, 7.8, 7.8, 3.9 Hz, 2 H) 1.5 (m, 2 H) 1.6 (m, 2 H) 1.7; LC/MS 217.2 (M−1).

後処理

  1. customReaction
  2. customseparate portions
  3. dissolutionto dissolve completely between additions
  4. stirringto stir
  5. temperaturewarm to RT overnight
  6. concentrationThe reaction is then concentrated to a sticky white solid
  7. dissolutionThis is dissolved in ethyl acetate (25 mL)/1 N HCl (25 mL)
  8. dry with materialThe organic solution is dried over anhydrous sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto afford the crude product as a yellow oil
  12. customThe crude product is chromatographed over silica eluting with 5→65% ethyl acetate in hexanes

出典と根拠

ORDレコード
ord-c86151cef6fd445e9bf1b33d58a57d9c
出典データセット
uspto-grants-2012_08
特許番号
US08252931B2

反応ノート

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