Triethylamine → HCID 56987970, compound
Reaction equation
[CH2:1]1[O:9][C:8]2[C:3](=[C:4]([C@H:10]([CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[CH2:11][C:12]([OH:14])=O)[CH:5]=[CH:6][CH:7]=2)[O:2]1.[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:22]=1[NH2:23].C(N(CC)CC)C>C(Cl)Cl>[F:20][C:21]1[CH:27]=[C:26]([F:28])[CH:25]=[C:24]([F:29])[C:22]=1[NH:23][C:12](=[O:14])[CH2:11][C@H:10]([C:4]1[CH:5]=[CH:6][CH:7]=[C:8]2[O:9][CH2:1][O:2][C:3]=12)[CH2:15][CH2:16][CH2:17][CH2:18][CH3:19]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
In the same manner as in Example 1, 0.86 g (3.25 mmol) of (R)-3-(2, 3-methylenedioxyphenyl) octanoic acid was converted into its acid chloride. This acid chloride was dissolved in 5 ml of methylene chloride and added dropwise to a solution of 571 mg (3.88 mmol) of 2, 4, 6-trifluoroaniline and 0.54 ml (3.9 mmol) of triethylamine in 15 ml of methylene chloride. The reaction mixture was stirred overnight, washed with water, dried over anhydrous magnesium sulfate and the solvent evaporated. The residue was chromatographed on a silica gel column, eluting with ethyl acetate/hexane (1/5) and recrystallized from a mixed solvent of hexane and a trace of ethyl acetate to give 1.11 g of (R)-N-(2, 4, 6-trifluorophenyl)-3-(2, 3-methylenedioxyphenyl) octanamide as white crystals. Yield, 87%.
Workup
- washwashed with water
- dry with materialdried over anhydrous magnesium sulfate
- customthe solvent evaporated
- customThe residue was chromatographed on a silica gel column
- washeluting with ethyl acetate/hexane (1/5)
- customrecrystallized from a mixed solvent of hexane
Sources & evidence
- ORD record
- ord-bbe34d007dbb445bab49d120f5a89aab
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05442060
Reaction notes
Loading…