Butyl iodide → (S)-6-{3-(N-tert-butoxycarbonyl-N-butylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

HRID 1845955노트

반응식

HRID 1845955 반응식
[H-].[Na+].[C:3]([O:7][C:8]([NH:10][C@H:11]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[N:24][CH:23]=[CH:22]3)(=[O:18])=[O:17])[CH2:12]1)=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH2:29](I)[CH2:30][CH2:31][CH3:32]>CN(C)C=O>[C:3]([O:7][C:8]([N:10]([C@H:11]1[CH2:15][CH2:14][N:13]([S:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[N:24][CH:23]=[CH:22]3)(=[O:18])=[O:17])[CH2:12]1)[CH2:29][CH2:30][CH2:31][CH3:32])=[O:9])([CH3:6])([CH3:4])[CH3:5]

참가 물질

5

반응물 3

HCID 10962Butyl iodideHCID 24758Sodium hydrideHCID 66727094(S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

생성물 1

HCID 66727449(S)-6-{3-(N-tert-butoxycarbonyl-N-butylamino)pyrrolidin-1-ylsulfonyl}isoquinoline

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

265 mg of sodium hydride was added with stirring under ice cooling to an N,N-dimethylformamide (10 mL) solution of 500 mg of (S)-6-{3-(tert-butoxycarbonylamino)pyrrolidin-1-ylsulfonyl}isoquinoline obtained in Step 1 of Example 10. After stirring in this state for 30 minutes, 0.8 mL of butyl iodide was added dropwise to the reaction solution, and the mixture was further stirred for 30 minutes for reaction. The reaction was terminated by the dropwise addition of water in small portions under ice cooling to the reaction solution. Then, 50 mL of water was added thereto, followed by three extractions with 50 mL of ether. The combined organic layer was washed with 100 mL of saturated saline and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated, and the obtained crude product was purified by silica gel column chromatography (acetone:hexane=1:1) to obtain 350 mg of the compound of interest as a colorless oil (61%).

후처리

  1. stirringthe mixture was further stirred for 30 minutes for reaction
  2. customThe reaction was terminated by the dropwise addition of water in small portions under ice cooling to the reaction solution
  3. additionThen, 50 mL of water was added
  4. extractionfollowed by three extractions with 50 mL of ether
  5. washThe combined organic layer was washed with 100 mL of saturated saline
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationAfter filtration
  8. concentrationthe filtrate was concentrated
  9. customthe obtained crude product
  10. customwas purified by silica gel column chromatography (acetone:hexane=1:1)

출처 및 근거

ORD 기록
ord-2fe4002b3f834819bd05c32bfaa1fa8d
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08951997B2

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