Trityl chloride → 1-((3R,4R)-3-hydroxy-4-(tritylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone

HRID 1666676노트

반응식

HRID 1666676 반응식
[NH2:1][C@H:2]1[C@H:6]([OH:7])[CH2:5][N:4]([C:8](=[O:21])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][C:17]([F:20])([F:19])[F:18])=[CH:12][CH:11]=2)[CH2:3]1.C(N(CC)CC)C.[C:29]1([C:35](Cl)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>C(Cl)(Cl)Cl.C1COCC1>[OH:7][C@H:6]1[C@H:2]([NH:1][C:35]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[CH2:3][N:4]([C:8](=[O:21])[CH2:9][C:10]2[CH:11]=[CH:12][C:13]([O:16][C:17]([F:18])([F:19])[F:20])=[CH:14][CH:15]=2)[CH2:5]1

참가 물질

6

반응물 3

HCID 6456Trityl chlorideHCID 8471TriethylamineHCID 579701111-((3R,4R)-3-amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone

생성물 1

HCID 674451821-((3R,4R)-3-hydroxy-4-(tritylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone수율 61.2%

시약·촉매·용매 2

HCID 6212Chloroform용매HCID 8028Tetrahydrofuran용매

실험 절차

1-((3R,4R)-3-Amino-4-hydroxypyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (1.0 g) was dissolved in chloroform (30 mL) and THF (10 mL), followed by addition of triethylamine (0.55 mL) and triphenylmethyl chloride (1.4 g), and the mixture was stirred at room temperature for 4 days. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography (silica gel, hexane/ethyl acetate=4:1-2:1) to obtain 1-((3R,4R)-3-hydroxy-4-(tritylamino)pyrrolidin-1-yl)-2-(4-trifluoromethoxyphenyl)ethanone (1.1 g).

후처리

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by column chromatography (silica gel, hexane/ethyl acetate=4:1-2:1)

출처 및 근거

ORD 기록
ord-f109ecd7c54347d1b0191eab99696a0c
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044068B2

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