반응 #163978

반응 방정식

2-MeTHF

T3P

2-MeTHF

Pyridine

NaOMe MeOH

2-MeTHF

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

5-amino-2,4-di-tert-butylphenyl methyl carbonate

→

N-(2,4-di-tert-butyl-5-hydroxyphenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamide

반응 조건

후처리

1. 1
   세척The T3P charged vessel was washed with 2-MeTHF (0.6 vol)
2. 2
   온도the resulting suspension was heated to 47.5+/−5.0° C.
3. 3
   온도Once complete, the resulting mixture was cooled to 20° C.+/−5° C
4. 4
   workup.ADDITIONto dilute the mixture
5. 5
   세척The reaction mixture was washed with water (10.0 vol) 2 times and 2-MeTHF (16.5 vol)
6. 6
   workup.ADDITIONwas charged to the reactor
7. 7
   기타Once complete, the reaction was quenched with 1.2N HCl/H2O (10.0 vol)
8. 8
   세척washed with 0.1N HCl/H2O (10.0 vol)
9. 9
   여과filtered
10. 10
    기타to remove any particulates
11. 11
    기타placed in a second reactor

실험 절차

4-Oxo-1,4-dihydroquinoline-3-carboxylic acid, 26, (1.0 eq) and 5-amino-2,4-di-tert-butylphenyl methyl carbonate, 32, (1.1 eq) were charged to a reactor. 2-MeTHF (4.0 vol, relative to the acid) was added followed by T3P® 50% solution in 2-MeTHF (1.7 eq). The T3P charged vessel was washed with 2-MeTHF (0.6 vol). Pyridine (2.0 eq) was then added, and the resulting suspension was heated to 47.5+/−5.0° C. and held at this temperature for 8 hours. A sample was taken and checked for completion by HPLC. Once complete, the resulting mixture was cooled to 20° C.+/−5° C. 2-MeTHF was added (12.5 vol) to dilute the mixture. The reaction mixture was washed with water (10.0 vol) 2 times and 2-MeTHF (16.5 vol) was charged to the reactor. This solution was charged with 30% w/w NaOMe/MeOH (1.7 equiv) to perform the methanolysis. The reaction was stirred at 25.0° C.+/−5.0° C. for no less than 1.0 hour, and checked for completion by HPLC. Once complete, the reaction was quenched with 1.2N HCl/H2O (10.0 vol), and washed with 0.1N HCl/H2O (10.0 vol). The organic solution was polish filtered to remove any particulates and placed in a second reactor.

출처