Reacción #603391

Ecuación de reacción

phenyl chloroformate

(S)-Phenyl(1-(3-chloro-2,6-difluorophenyl)but-3-en-1-yl)carbamate

HCl

→

desired product

Rendimiento 40.0%

(S)-Phenyl(1-(3-chloro-2,6-difluorophenyl)-3-oxopropyl)carbamate

Rendimiento 40.0%

Disolventes

ACN

EtOAc

MeOH

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.WAITAfter 1 h
2. 2
   Concentraciónthe reaction mixture was concentrated
3. 3
   Otrodried under vacuum
4. 4
   Otroto obtain a pale yellow solid
5. 5
   OtroThe above reaction mixture
6. 6
   Temperaturawas cooled to 0° C
7. 7
   Otrothe resulting reaction
8. 8
   workup.STIRRINGwas stirred at 0° C. for 1 h
9. 9
   Lavadowashed with water
10. 10
    OtroThe crude product was then purified by silica gel chromatography

Procedimiento

(S)-Phenyl(1-(3-chloro-2,6-difluorophenyl)but-3-en-1-yl)carbamate: To a solution of crude Intermediate 17B (1.17 g, 3.64 mmol) in MeOH (10 mL) was added HCl (5 mL, 20.00 mmol) and the reaction was stirred at rt for 1 h. After 1 h, the reaction mixture was concentrated and dried under vacuum to obtain a pale yellow solid. The solid was dissolved in ACN (25 mL) followed by addition of TEA (1.520 mL, 10.91 mmol). The above reaction mixture was cooled to 0° C. To this mixture was added phenyl chloroformate (0.502 mL, 4.00 mmol) dropwise and the resulting reaction was stirred at 0° C. for 1 h. The reaction mixture was then diluted with EtOAc and washed with water followed by brine. The crude product was then purified by silica gel chromatography to give the desired product (490 mg, 40%) as clear oil. MS (ESI) m/z: 338.1 (M+H)+.

Fuente