Triethylamine → 2-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amide

HRID 23576

반응식

HRID 23576 반응식
[CH2:1]([NH:4][C@@H:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[CH:2]=[CH2:3].[N:18]1([S:23]([C:26]2[CH:27]=[C:28]([CH:32]([CH2:36][CH:37]=[CH2:38])[C:33](O)=[O:34])[CH:29]=[CH:30][CH:31]=2)(=[O:25])=[O:24])[CH2:22][CH2:21][CH2:20][CH2:19]1.[I-].ClC1C=CC=C[N+]=1C.C(N(CC)CC)C>ClCCl.C(OCC)(=O)C.O>[CH2:1]([N:4]([C@@H:5]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][CH2:8]1)[C:33](=[O:34])[CH:32]([C:28]1[CH:29]=[CH:30][CH:31]=[C:26]([S:23]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)(=[O:25])=[O:24])[CH:27]=1)[CH2:36][CH:37]=[CH2:38])[CH:2]=[CH2:3]

참가 물질

8

반응물 4

HCID 8471TriethylamineHCID 1670692-Chloro-1-methylpyridinium iodideHCID 225731942-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acidHCID 69731210(S)-N-(1-Phenyl-2-(pyrrolidin-1-YL)ethyl)prop-2-EN-1-amine

생성물 1

HCID 697304392-[3-(Pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amide수율 92.9%

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a stirred solution of allyl-(1-(S)-phenyl-2-pyrrolidin-1-yl-ethyl)-amine (1.00 g, 4.34 mmol) in dichloromethane (22 cm3) at ambient temperature was added 2-[3-(pyrrolidine-1-sulfonyl)-phenyl]-pent-4-enoic acid (1.34 g, 4.34 mmol) followed by 2-Chloro-1-methylpyridinium iodide (2.22 g, 8.68 mmol) and triethylamine (1.82 cm3, 13.0 mmol) to afford a yellow slurry. The mixture was stirred at ambient temperature for 44 hours to afford a brown solution. The solution was diluted with ethyl acetate (50 cm3) and poured into water (100 cm3). The aqueous was extracted with ethyl acetate (3×30 cm3) and the combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3), dried over sodium sulfate, vacuum filtered and the volatile fractions removed in vacuo to a crude brown oil. The crude product was purified by column chromatography (silica, eluting with dichloromethane-methanol 99:1 to 95:5 to afford the title compound as a tan viscous oil (2.10, 92.9%) with a positive ion ESI (M+H)+522.3.

후처리

  1. customto afford a yellow slurry
  2. customto afford a brown solution
  3. extractionThe aqueous was extracted with ethyl acetate (3×30 cm3)
  4. washthe combined ethyl acetate extracts were washed with 1M sodium bicarbonate (2×50 cm3), brine (1×50 cm3)
  5. dry with materialdried over sodium sulfate, vacuum
  6. filtrationfiltered
  7. customthe volatile fractions removed in vacuo to a crude brown oil
  8. customThe crude product was purified by column chromatography (silica
  9. washeluting with dichloromethane-methanol 99:1 to 95:5

출처 및 근거

ORD 기록
ord-12d3abfc341b4ce6bea39f454d37a6fa
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06852713B2

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