tert-Butanol → (6-Fluoro-quinolin-3-yl)carbamic acid tert-butyl ester
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6](C(O)=O)=[CH:5]2.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:22])C=CC=CC=1.C([N:35]([CH:38](C)C)CC)(C)C.[C:41]([OH:45])([CH3:44])([CH3:43])[CH3:42]>>[C:41]([O:45][C:38](=[O:22])[NH:35][C:6]1[CH:7]=[N:8][C:9]2[C:4]([CH:5]=1)=[CH:3][C:2]([F:1])=[CH:11][CH:10]=2)([CH3:44])([CH3:43])[CH3:42]Participants
5
Procedure
A solution of 6-fluoro-quinoline-3-carboxylic acid (1.7 g, 8.89 mmol), diphenylphosphoryl azide (2.3 mL, 10.7 mmol) and diisopropylethylamine (4.65 mL, 26.67 mmol) in t-butanol (40 mL) was heated at reflux for 1 hour. The solution was cooled to room temperature, and the solvent was evaporated in vacuo. The residue was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was dried over sodium sulfate, and the product was preabsorbed onto silica gel. Purification by flash chromatography, using a gradient of ethyl acetate (0% to 30%) in heptane as the eluant, to give the product as a colorless solid, 1.3 g (56%). MS: m/z 263.0 (MH+).
Workup
- temperatureat reflux for 1 hour
- customthe solvent was evaporated in vacuo
- customThe residue was partitioned between aqueous sodium bicarbonate and dichloromethane
- dry with materialThe organic layer was dried over sodium sulfate
- customthe product was preabsorbed onto silica gel
- customPurification by flash chromatography
Sources & evidence
- ORD record
- ord-9d7f1725531c4c06bd11f28bccde49b1
- Source dataset
- uspto-grants-2013_03
- Patent number
- US08394828B2
Reaction notes
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