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 1700892Notes

Reaction equation

[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]

Participants

Conditions

Temperature: 50 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-51db08b6f4fc47dda93f2246e3f966f9
Source dataset: uspto-grants-2002_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06350892B1

Reaction notes

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