2,2-Dimethyl-3-acetyloxypropionyl chloride → (3S)-1-Cbz-3-[cyclohexyl(acetyloxypivaloyl)amino]pyrrolidine

HRID 1670008ノート

反応式

HRID 1670008 の反応式
[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([NH:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[CH2:12]1)([O:3][CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:2].[CH3:23][C:24]([CH3:33])([CH2:28][O:29][C:30](=[O:32])[CH3:31])[C:25](Cl)=[O:26]>CN(C1C=CN=CC=1)C.C1COCC1>[C:1]([N:11]1[CH2:15][CH2:14][C@H:13]([N:16]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:25](=[O:26])[C:24]([CH3:33])([CH3:23])[CH2:28][O:29][C:30](=[O:32])[CH3:31])[CH2:12]1)([O:3][CH2:4][C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:2]

参加物

5

反応物 2

HCID 111946632,2-Dimethyl-3-acetyloxypropionyl chlorideHCID 67343263HCID 67343263、化合物

生成物 1

HCID 67345539(3S)-1-Cbz-3-[cyclohexyl(acetyloxypivaloyl)amino]pyrrolidine収率 63%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

To the mixture of (3S)-1-Cbz-3-(cyclohexylamino)pyrrolidine (3.0 g, 10 mmol), TEA (15 mL), and DMAP (1.25 g, 10 mmol) in THF (15 mL) was added 2,2-dimethyl-3-acetyloxypropionyl chloride (3.58 g, 20 mmol) prepared in Step A. After the reaction mixture was refluxed for 48 h (90-110° C.), the solvent was removed, and the residue was diluted with an aqueous NaHCO3 solution was added to the residue. The organic material was extracted with EtOAc, and the extracts were washed by 1N HCl, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chomatography (EtOAc/Hex=1/2) to give the title compound (2.80 g, 62.9%).

後処理

  1. customthe solvent was removed
  2. additionthe residue was diluted with an aqueous NaHCO3 solution
  3. additionwas added to the residue
  4. extractionThe organic material was extracted with EtOAc
  5. washthe extracts were washed by 1N HCl
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by column chomatography (EtOAc/Hex=1/2)

出典と根拠

ORDレコード
ord-f6215a36d3434bccbb8d9d08471945b0
出典データセット
uspto-grants-2011_08
特許番号
US07989634B2

反応ノート

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