Hydrogen Peroxide → (S)-2-((R)-3-isopropyl-2-oxopyrrolidin-1-yl)-4-phenylbutanoic acid

HRID 132936

反応式

HRID 132936 の反応式
C(O[C@H:5]1[CH2:9][N:8](C(OC(C)(C)C)=O)[C@@H:7]([CH2:17][OH:18])[CH2:6]1)C=C.[CH:19]([C@@H:22]([CH2:26][CH:27]=C)[C:23]([OH:25])=O)([CH3:21])[CH3:20].[Li+].[OH-:30].OO>C1COCC1.O>[CH:19]([C@H:22]1[CH2:26][CH2:27][N:8]([C@@H:7]([CH2:6][CH2:5][C:9]2[CH:17]=[CH:7][CH:6]=[CH:5][CH:9]=2)[C:17]([OH:18])=[O:30])[C:23]1=[O:25])([CH3:20])[CH3:21]

参加物

7

反応物 4

HCID 784Hydrogen PeroxideHCID 3939Lithium HydroxideHCID 6915842(R)-2-isopropylpent-4-enoic acidHCID 67315914(2R,4R)-tert-butyl 4-(allyloxy)-2-(hydroxymethyl)pyrrolidine-1-carboxylate

生成物 1

HCID 69193934(S)-2-((R)-3-isopropyl-2-oxopyrrolidin-1-yl)-4-phenylbutanoic acid

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

Step D (3): (R)-2-isopropylpent-4-enoic acid. To a solution of the compound of step D (2) (1.08 g, 3.59 mmol) in THF (14.4 mL) was added water (3.59 mL), and the mixture cooled to 0° C. A solution of LiOH (172.5 mg, 7.20 mmol) and 30% H2O2 (3.26 mL) in water (11.2 mL) was added, and the combined mixture stirred for 10 minutes at 0° C. The ice bath was removed, and the reaction was allowed to continue for 1 h at rt. A solution of sodium sulfite (3.63 g) was added, and the reaction stirred for 10 min. Saturated sodium carbonate solution was added, and the reaction was extracted with methylene chloride. The aqueous layer was acidified to pH 1 with 6 N HCl, and extracted 3 times with diethyl ether. The combined ether layers were washed with brine, and dried over MgSO4. The extract was filtered, and concentrated in vacuo to afford the desired product.

後処理

  1. customThe ice bath was removed
  2. waitto continue for 1 h at rt
  3. additionA solution of sodium sulfite (3.63 g) was added
  4. stirringthe reaction stirred for 10 min
  5. additionSaturated sodium carbonate solution was added
  6. extractionthe reaction was extracted with methylene chloride
  7. extractionextracted 3 times with diethyl ether
  8. washThe combined ether layers were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationThe extract was filtered
  11. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-283a997f1521485da8e04a718d140aab
出典データセット
uspto-grants-2008_06
特許番号
US07388007B2

関連ノート

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