Реакция #603391

Уравнение реакции

phenyl chloroformate

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

HCl

→

desired product

Выход 40.0%

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

Выход 40.0%

Растворители

ACN

EtOAc

MeOH

Условия реакции

Обработка

1. 1
   workup.WAITAfter 1 h
2. 2
   Концентрированиеthe reaction mixture was concentrated
3. 3
   Другоеdried under vacuum
4. 4
   Другоеto obtain a pale yellow solid
5. 5
   ДругоеThe above reaction mixture
6. 6
   Температураwas cooled to 0° C
7. 7
   Другоеthe resulting reaction
8. 8
   workup.STIRRINGwas stirred at 0° C. for 1 h
9. 9
   Промывкаwashed with water
10. 10
    ДругоеThe crude product was then purified by silica gel chromatography

Методика

(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)+.

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