Isobutyryl chloride → (3S)-1-Cbz-3-[cyclohexyl(isobutyryl)amino]pyrrolidine

HRID 1669999ノート

反応式

HRID 1669999 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].[C:23](Cl)(=[O:27])[CH:24]([CH3:26])[CH3:25]>C(Cl)Cl>[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:23](=[O:27])[CH:24]([CH3:26])[CH3:25])[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

4

反応物 2

HCID 62325Isobutyryl chlorideHCID 67343263HCID 67343263、化合物

生成物 1

HCID 67345617(3S)-1-Cbz-3-[cyclohexyl(isobutyryl)amino]pyrrolidine収率 96.7%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of (3S)-1-Cbz-3-(cyclohexylamino)pyrolidine (4.75 g, 15.1 mmol) and TEA (4.26 mL, 30.2 mmol) in DCM (50 mL) was added dropwise isobutyryl chloride (1.15 mL, 60.3 mmol). The reaction mixture was stirred at rt for 12 h and quenched with 1N HCl solution. The organic material was extracted with DCM (50 mL×2) followed by EtOAc (50 mL×2), and the extracts were washed with a saline, dried over MgSO4, and concentrated in vacuo. The residue was purified by column chomatography (EtOAc/Hex=1/3) to give the title compound (5.40 g, 96.7%).

後処理

  1. customquenched with 1N HCl solution
  2. extractionThe organic material was extracted with DCM (50 mL×2)
  3. washthe extracts were washed with a saline
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chomatography (EtOAc/Hex=1/3)

出典と根拠

ORDレコード
ord-e207be9dbeb442b6affe3badd3719aae
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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