Ethyl Acetate → Methyl 3-[(dipropylamino)carbonyl]-5-(4-methyl-1,3-oxazol-2-yl)benzoate
Reaction equation
[NH2:1][C:2]([C:4]1[CH:5]=[C:6]([CH:11]=[C:12]([C:14]([N:16]([CH2:20][CH2:21][CH3:22])[CH2:17][CH2:18][CH3:19])=[O:15])[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:3].[C:23](=O)([O-])[O-].[K+].[K+].C(O[CH2:33][CH3:34])(=O)C>>[CH2:20]([N:16]([CH2:17][CH2:18][CH3:19])[C:14]([C:12]1[CH:11]=[C:6]([CH:5]=[C:4]([C:2]2[O:3][CH:23]=[C:33]([CH3:34])[N:1]=2)[CH:13]=1)[C:7]([O:9][CH3:10])=[O:8])=[O:15])[CH2:21][CH3:22]Participants
Procedure
A stirred solution of methyl 3-(aminocarbonyl)-5-[(dipropylamino)carbonyl]benzoate (200 mg, 0.65 mmol) chloroacetone (10 mL, 93 mmol) and potassium carbonate (90 mg, 0.65 mmol) was refluxed for 18 h. The reaction mixture was cooled to room temperature, diluted with ethyl acetate, washed with 2 N sodium hydroxide (2×50 mL), and saturated sodium chloride, dried (magnesium sulfate), and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes) provided methyl 3-[(dipropylamino)carbonyl]-5-(4-methyl-1,3-oxazol-2-yl)benzoate (119 mg): 1H NMR (300 MHz, CDCl3) δ 8.70 (d, J=1 Hz, 1H), 8.20 (d, J=1 Hz, 1H), 8.09 (d, J=1 Hz, 1H), 7.48 (s, 1H), 3.96 (s, 3H), 3.46 (d, J=7 Hz, 2H), 3.16 (t, J=7 Hz, 2H), 2.26 (s, 3H), 1.71 (d, J=7 Hz, 2H), 1.54 (d, J=7 Hz, 2H), 1.00 (t, J=7 Hz, 3H), 0.74 (t, J=7 Hz, 3H); ESI MS m/z 345 [M+H]+.
Workup
- washwashed with 2 N sodium hydroxide (2×50 mL), and saturated sodium chloride
- dry with materialdried (magnesium sulfate)
- concentrationconcentrated under reduced pressure
- customPurification by flash column chromatography (silica, 1:1 ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-79c0b5d6479547ac8d0e14f72284f038
- Source dataset
- uspto-grants-2007_02
- Patent number
- US07176242B2
Reaction notes
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