tert-Butanol → N-tert-butoxycarbonyl-3-methoxy-2-methylaniline
Reaction equation
C([N:3](CC)CC)C.[CH3:8][O:9][C:10]1[C:11]([CH3:19])=[C:12]([CH:16]=[CH:17][CH:18]=1)C(O)=O.C[C@H]1[C@]2(O)[C@H]3[C@](O)(CC(COC(C)=O)=C[C@H]2[C@@H:24]2[C:25](C)(C)[C@:23]2([O:47][C:48](CC2C=CC=CC=2)=[O:49])[CH2:22]1)C(=O)C(C)=C3.CC(O)(C)C>C1(C)C=CC=CC=1>[C:23]([O:47][C:48]([NH:3][C:12]1[CH:16]=[CH:17][CH:18]=[C:10]([O:9][CH3:8])[C:11]=1[CH3:19])=[O:49])([CH3:25])([CH3:24])[CH3:22]Participants
6
Conditions
- Temperature
- 70 °C
Procedure
Triethylamine (42.4 mL, 302 mmol) was added to a suspension of 3-methoxy-2-methylbenzoic acid (45.6 g, 274 mmol) in dry toluene (800 mL). A clear solution was obtained. Then, dppa (65.4 mL, 302 mmol) in toluene (100 mL) was slowly added. After 1 h at room temperature, the reaction mixture was successively heated at 50° C. for 0.5 h, at 70° C. for 0.5 h then at 100° C. for 1 h. To this solution, t-BuOH (30.5 g, 411 mmol) in toluene (40 mL) was added at 100° C. and the resulting mixture was refluxed for 7 h. The solution was cooled to room temperature then successively washed with water, 0.5 N HCl, 0.5 N NaOH and brine, dried (Na2SO4), and evaporated to give 67 g of the target product: m/z=237 (M)+.
Workup
- customA clear solution was obtained
- waitat 100° C. for 1 h
- temperaturethe resulting mixture was refluxed for 7 h
- temperatureThe solution was cooled to room temperature
- washthen successively washed with water, 0.5 N HCl, 0.5 N NaOH and brine
- dry with materialdried (Na2SO4)
- customevaporated
Sources & evidence
- ORD record
- ord-ed5136b63fd44a91a26b402b1e30fb0e
- Source dataset
- uspto-grants-2014_06
- Patent number
- US08741926B2
Reaction notes
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