3-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester → 3-Allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester

HRID 722740ノート

反応式

HRID 722740 の反応式
[CH2:1]([Mg]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:10]([O:14][C:15](=[O:27])[CH2:16][CH:17]([NH:20][C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[CH:18]=[O:19])([CH3:13])([CH3:12])[CH3:11]>C1COCC1>[C:10]([O:14][C:15](=[O:27])[CH2:16][CH:17]([NH:20][C:21]([O:23][CH2:24][CH:25]=[CH2:26])=[O:22])[CH:18]([OH:19])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)([CH3:13])([CH3:12])[CH3:11]

参加物

4

反応物 2

HCID 184657153-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl esterHCID 178418336HCID 178418336、化合物

生成物 1

HCID 235714393-Allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a solution of benzylmagnesium chloride (20 mL, 20 mmol) in THF at −78° C. is added dropwise a 0° C. solution of 3-allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester, 102, (5.14 g, 20 mmol) in THF (100 mL). Once the addition is complete, the solution is allowed to warm to 0° C. over 30 minutes then the reaction mixture is poured into a beaker of crushed ice. The solution is extracted ×3 with CH2Cl2 (100 mL), the organic layers combined, dried over Na2SO4 and concentrated in vacuo to afford the desired product which is used without further purification.

後処理

  1. additionOnce the addition
  2. additionthe reaction mixture is poured into a beaker of crushed ice
  3. extractionThe solution is extracted ×3 with CH2Cl2 (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-01b12a2d42934b47932fb8be5ace632d
出典データセット
uspto-grants-2006_11
特許番号
US07138395B2

反応ノート

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