تفاعل #1780409

معادلة التفاعل

tert-Butyl(±)-[(4aR*,6S*,8aS*)-8a-(2-fluorophenyl)-6-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]carbamate

perfluorobutanesulfonyl fluoride

triethylamine

Perfluorobutanesulfonyl fluoride

triethylamine

→

title compound

tert-butyl(±)-[(4aR*,6R*,8aS*)-6-fluoro-8a-(2-fluorophenyl)-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]carbamate

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   workup.ADDITIONAfter completion of the addition
2. 2
   workup.STIRRINGfurther stirred for 24 hours
3. 3
   workup.STIRRINGby further stirring
4. 4
   درجة الحرارةwith heating
5. 5
   درجة الحرارةunder reflux for eight hours
6. 6
   درجة الحرارةThe reaction solution was cooled to room temperature
7. 7
   تركيزconcentrated under reduced pressure
8. 8
   أخرىThen, the residue was purified by silica gel column chromatography

الإجراء التجريبي

tert-Butyl(±)-[(4aR*,6S*,8aS*)-8a-(2-fluorophenyl)-6-hydroxy-4a,5,6,7,8,8a-hexahydro-4H-benzo[d][1,3]thiazin-2-yl]carbamate obtained in Preparation Example 63-(4) (1.5 g) was dissolved in THF. Then, perfluorobutanesulfonyl fluoride (1.36 mL, specific gravity: 1.682 g/cm3), a triethylamine-trihydrofluoric acid complex (1.23 mL, specific gravity: 0.989 g/cm3) and triethylamine (3.15 mL, specific gravity: 0.73 g/cm3) were sequentially added at room temperature. After completion of the addition, the mixture was stirred for 16 hours. The mixture was heated to 50° C. and further stirred for 24 hours. Perfluorobutanesulfonyl fluoride (0.68 mL), a triethylamine-trihydrofluoric acid complex (0.62 mL) and triethylamine (1.58 mL) were further sequentially added to the mixture, followed by further stirring with heating under reflux for eight hours. The reaction solution was cooled to room temperature and concentrated under reduced pressure. Then, the residue was purified by silica gel column chromatography to obtain the title compound (106 mg).

المصدر