tert-Butanol → [2-(4-Chloro-2-methoxyphenyl)-4-methylthiazol-5-yl]carbamic acid tert-butyl ester
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10](C(O)=O)=[C:11]([CH3:13])[N:12]=2)=[C:4]([O:17][CH3:18])[CH:3]=1.C([N:21]([CH2:24]C)CC)C.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:33])C=CC=CC=1.[C:43]([OH:47])([CH3:46])([CH3:45])[CH3:44]>>[C:43]([O:47][C:24](=[O:33])[NH:21][C:10]1[S:9][C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][C:4]=2[O:17][CH3:18])=[N:12][C:11]=1[CH3:13])([CH3:46])([CH3:45])[CH3:44]Participants
5
Procedure
In tert-butanol (10 ml), 2-(4-chloro-2-methoxyphenyl)-4-methylthiazole-5-carboxylic acid (567 mg, 2.00 mmol) prepared in Example 7-1 was suspended, and triethylamine (243 mg, 2.40 mmol) and then diphenylphosphoryl azide (605 mg, 2.20 mmol) were added thereto. The mixture was heated under reflux for 16 hours. After being allowed to cool, the mixture was concentrated under a reduced pressure, and dissolved in chloroform. The resulting solution was washed with a saturated sodium bicarbonate solution, and then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1) to give the title compound (1.04 g, quantitative) as a white powder.
Workup
- temperatureThe mixture was heated
- temperatureunder reflux for 16 hours
- temperatureto cool
- concentrationthe mixture was concentrated under a reduced pressure
- dissolutiondissolved in chloroform
- washThe resulting solution was washed with a saturated sodium bicarbonate solution
- dry with materialdried over anhydrous magnesium sulfate
- concentrationconcentrated
- customThe concentrate was purified by silica gel column chromatography (n-hexane:ethyl acetate=1:1)
Sources & evidence
- ORD record
- ord-dc4e73fccac841c98ce966b7d771b257
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09200008B2
Reaction notes
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