Tetrahydrofuran → (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

HRID 227940ノート

反応式

HRID 227940 の反応式
[CH2:1]([O:8][C:9]([N:11]([CH2:32][C:33]([N:35]1[CH2:39][C@@H:38]([F:40])[CH2:37][C@H:36]1[C:41]#[N:42])=[O:34])[C:12]12[CH2:19][CH2:18][C:15]([C:20](ON3C4C=CC=CC=4N=N3)=[O:21])([CH2:16][CH2:17]1)[CH2:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:43]1[CH2:47][CH2:46][CH2:45][CH2:44]1.O1CCC[CH2:49]1>>[CH2:1]([O:8][C:9]([N:11]([CH2:32][C:33]([N:35]1[CH2:39][C@@H:38]([F:40])[CH2:37][C@H:36]1[C:41]#[N:42])=[O:34])[C:12]12[CH2:13][CH2:14][C:15]([C:20]([N:43]3[CH2:47][CH2:46][CH2:45][CH2:44][CH2:49]3)=[O:21])([CH2:18][CH2:19]1)[CH2:16][CH2:17]2)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 3

HCID 8028TetrahydrofuranHCID 31268PyrrolidineHCID 57756828(2S,4S)-1-[(N-benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

生成物 1

HCID 68844891(2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile

実験手順

(2S,4S)-1-[[N-Benzyloxycarbonyl-N-[4-(benzotriazol-1-yl)oxycarbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (20.0 mg) and pyrrolidine (4.4 μL) were dissolved in tetrahydrofuran (0.4 mL) and the mixture was stirred at room temperature for 25 minutes. The solvent was removed under reduced pressure and the residue was dissolved in dichloromethane. The organic layer washed sequentially with 0.1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated brine. The organic layer was then dried over anhydrous sodium sulfate and was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (eluant:ethyl acetate:methanol=20:1) to give (2S,4S)-1-[[N-benzyloxycarbonyl-N-[4-(piperidin-1-yl)carbonylbicyclo[2.2.2]oct-1-yl]amino]acetyl]-4-fluoropyrrolidine-2-carbonitrile (16.0 mg).

後処理

  1. customThe solvent was removed under reduced pressure
  2. dissolutionthe residue was dissolved in dichloromethane
  3. washThe organic layer washed sequentially with 0.1 N aqueous hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated brine
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  5. concentrationwas concentrated under reduced pressure
  6. customThe resulting residue was purified by silica gel chromatography (eluant:ethyl acetate:methanol=20:1)

出典と根拠

ORDレコード
ord-d38ef3ca138349b3840f0c6f352da442
出典データセット
uspto-grants-2009_07
特許番号
US07560569B2

反応ノート

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