4-[N-Dodecyl-N-[2-[4-(3,3-Dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester → 4-[N-dodecyl-N-[2-[4-(3oxo-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]butanoic acid, ethyl ester
Reaction equation
[CH2:1]([N:13]([CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:14][CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25](OC)([O:30]C)[C:26]([F:29])([F:28])[F:27])=[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]>FC(F)(F)C(O)=O>[CH2:1]([N:13]([CH2:34][CH2:35][CH2:36][C:37]([O:39][CH2:40][CH3:41])=[O:38])[CH2:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([CH2:23][CH2:24][C:25](=[O:30])[C:26]([F:27])([F:28])[F:29])=[CH:21][CH:22]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12]Participants
3
Reactant 1
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-[N-Dodecyl-N-[2-[4-(3,3-dimethoxy-4,4,4-trifluorobut-1-yl)phenoxy]ethyl]amino]-butanoic acid, ethyl ester (315 mg, 0.53 mmol) in trifluoroacetic acid (5 ml) was heated to 70° C. for 2 h, and then concentrated in vacuo. The residue was diluted with ethyl acetate (100 ml), washed with sat. sodium bicarbonate (30 ml), brine (30 ml), dried over magnesium sulfate and concentrated in vacuo. The residue was chromatographed on silica gel (Hexane/ethyl acetate 2:1 to 1.5:1) to afford the title compound (224 mg, 77%) as a colorless oil.
Workup
- concentrationconcentrated in vacuo
- additionThe residue was diluted with ethyl acetate (100 ml)
- washwashed with sat. sodium bicarbonate (30 ml), brine (30 ml)
- dry with materialdried over magnesium sulfate
- concentrationconcentrated in vacuo
- customThe residue was chromatographed on silica gel (Hexane/ethyl acetate 2:1 to 1.5:1)
Sources & evidence
- ORD record
- ord-4d7f83a0926246989cc04b377d19ae57
- Source dataset
- uspto-grants-2002_02
- Patent number
- US06350892B1
Reaction notes
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