Tetrahydrofuran → (4'-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)acetic acid methyl ester

HRID 546970노트

반응식

HRID 546970 반응식
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.[CH3:24][O:25][C:26](=[O:66])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([CH2:62][CH3:63])([C:43]3[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]4([O:56][Si](C)(C)C)[CH2:55][CH2:54][CH2:53][CH2:52]4)=[C:45]([CH3:61])[CH:44]=3)[CH2:41][CH3:42])=[CH:36][C:35]=2[CH3:64])=[CH:30][C:29]=1[F:65].[Cl-].[NH4+]>>[CH3:24][O:25][C:26](=[O:66])[CH2:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[CH:39]=[CH:38][C:37]([C:40]([CH2:62][CH3:63])([C:43]3[CH:48]=[CH:47][C:46]([C:49]#[C:50][C:51]4([OH:56])[CH2:55][CH2:54][CH2:53][CH2:52]4)=[C:45]([CH3:61])[CH:44]=3)[CH2:41][CH3:42])=[CH:36][C:35]=2[CH3:64])=[CH:30][C:29]=1[F:65]

참가 물질

5

반응물 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57709128HCID 57709128, 화합물

생성물 1

HCID 57708971(4'-{1-Ethyl-1-[4-(1-hydroxy-cyclopentylethynyl)-3-methyl-phenyl]-propyl}-3-fluoro-2'-methyl-biphenyl-4-yl)acetic acid methyl ester수율 88.9%

실험 절차

A 1 M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.105 mL, 0.105 mmol) was added to (4′-{1-ethyl-1-[3-methyl-4-(1-trimethylsilanyloxy-cyclopentylethynyl)-phenyl]-propyl}-3-fluoro-2′-methyl-biphenyl-4-yl)acetic acid methyl ester (Example 93-(1); 52.6 mg, 0.0878 mmol), and the mixture was stirred for 40 minutes. A saturated aqueous ammonium chloride solution was added to the reaction mixture, followed by extraction with diethyl ether. The organic layer was washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography (20% ethyl acetate/hexane) to give the title compound (41.1 mg, 88%).

후처리

  1. extractionfollowed by extraction with diethyl ether
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel chromatography (20% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-8abd2b17e3974a2fa9722a57c9542997
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07935688B2

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