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

HRID 1669999노트

반응식

HRID 1669999 반응식
[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]

참가 물질

4

반응물 2

HCID 62325Isobutyryl chlorideHCID 67343263HCID 67343263, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-e207be9dbeb442b6affe3badd3719aae
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989634B2

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