Reaktion #163964

Reaktionsgleichung

T3P

[5-amino-4-tert-butyl-2-(2-methoxycarbonyloxy-1,1-dimethyl-ethyl)phenyl]methyl carbonate

4-oxo-1,4-dihydroquinoline-3-carboxylic acid

pyridine

Sodium methoxide

→

Compound 27

N-(2-tert-butyl-5-hydroxy-4-(1-hydroxy-2-methylpropan-2-yl)phenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

Lösungsmittel

2-MeTHF

water

2-MeTHF

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturAfter cooling to ambient temperature
2. 2
   SonstigeThe organic phase was separated
3. 3
   Waschenagain washed with water
4. 4
   SonstigeThe reaction was quenched with 1N HCl
5. 5
   Sonstigeafter separating the phases
6. 6
   Waschenthe organic phase was washed with 0.1N HCl
7. 7
   Sonstigethan dried in vacuo

Vorschrift

To a mixture of [5-amino-4-tert-butyl-2-(2-methoxycarbonyloxy-1,1-dimethyl-ethyl)phenyl]methyl carbonate (103 mg, 0.29 mmol), 4-oxo-1,4-dihydroquinoline-3-carboxylic acid (50 mg, 0.26 mmol), and pyridine (42 mg, 0.53 mmol) in 2-MeTHF (3.0 mL) was charged T3P as a 50 wt % solution in 2-MeTHF (286 mg, 0.45 mmol). The mixture was heated to 50° C. for 18 h. After cooling to ambient temperature, the mixture was diluted with water. The organic phase was separated and again washed with water. Sodium methoxide (39 mg, 0.72 mmol) was charged to the organic phase and the solution stirred for 2 hours. The reaction was quenched with 1N HCl, and after separating the phases, the organic phase was washed with 0.1N HCl. The organic phase was than dried in vacuo to yield Compound 27 as a solid. The 1H-NMR spectrum was consistent with that reported above.

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