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 546970ノート

反応式

HRID 546970 の反応式
[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]

参加物

5

反応物 4

HCID 8028TetrahydrofuranHCID 25517Ammonium ChlorideHCID 2724141Tetrabutylammonium FluorideHCID 57709128HCID 57709128、化合物

生成物 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 ester収率 88.9%

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-8abd2b17e3974a2fa9722a57c9542997
出典データセット
uspto-grants-2011_05
特許番号
US07935688B2

反応ノート

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