Tetrahydrofuran → 4-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino] butanoic acid, ethyl ester

HRID 1383911ノート

反応式

HRID 1383911 の反応式
[CH2:1]([N:13]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](I)=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[F:32][C:33]([F:39])([F:38])[CH:34]([OH:37])[CH:35]=[CH2:36].O1CCCC1.C(=O)(O)[O-].[Na+]>CN(C)C=O.O.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]([N:13]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20](/[CH:36]=[CH:35]/[CH:34]([OH:37])[C:33]([F:39])([F:38])[F:32])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12].[CH2:1]([N:13]([CH2:24][CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:36][CH2:35][C:34](=[O:37])[C:33]([F:39])([F:38])[F:32])=[CH:19][CH:18]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]

参加物

10

反応物 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 132629561,1,1-Trifluorobut-3-en-2-olHCID 867571204-[N-dodecyl-N-2-[4-iodophenoxy]ethylamino]butanoic acid, ethyl ester

生成物 2

HCID 867571214-[N-dodecyl-N-2-[4-(E)-[3-hydroxy-4,4,4-trifluorobut-1-en-1-yl]phenoxy]ethylamino] butanoic acid, ethyl ester収率 78%HCID 867571224-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester収率 6.6%

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 16212273Tetrabutylammonium chloride hydrate触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

To a solution of 4-[N-dodecyl-N-2-[4-iodophenoxy]ethylamino]butanoic acid, ethyl ester (4.5 g, 8.3 mmol) and 4,4,4-trifluorobut-1-en-3-ol (Pegolotti, J. A. and Young, W. G. J. Amer. Chem. Soc., 1961, 83, 3251) (complex with 1 tetrahydrofuran, 3.3 g, 16.6 mmol) in N, N-dimethylformamide (17 ml) were added sodium bicarbonate (1.75 g, 20.8 mmol), tetrabutyl ammonium chloride hydrate (2.5 g, 8.32 mmol) and palladium (II) acetate (56 mg, 0.25 mmol). The resulting mixture was stirred at 50° C. for 24 h, and then diluted with ethyl acetate (300 ml), washed with brine (100 ml), sat. aq. sodium thiosulfate (2×100 ml), brine (2×100 ml), dried over sodium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (Hexane/ethyl acetate 4:1 to 2:1) to afford the title compound (3.5 g, 78%) as a colorless oil and 0.3 g (6.6%) of 4-[N-Dodecyl-N-[2-[4-(4,4,4-trifluoro-3-oxo-but-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester.

後処理

  1. washwashed with brine (100 ml), sat. aq. sodium thiosulfate (2×100 ml), brine (2×100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was chromatographed on silica gel (Hexane/ethyl acetate 4:1 to 2:1)

出典と根拠

ORDレコード
ord-7aea43766a1e4784a076adcaa6a51ef9
出典データセット
uspto-grants-2001_07
特許番号
US06255496B1

反応ノート

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