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

HRID 1670008노트

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HRID 1670008 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].[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]

참가 물질

5

반응물 2

HCID 111946632,2-Dimethyl-3-acetyloxypropionyl chlorideHCID 67343263HCID 67343263, 화합물

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-f6215a36d3434bccbb8d9d08471945b0
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07989634B2

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