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

(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)+.

1. waitAfter 1 h
2. concentrationthe reaction mixture was concentrated
3. customdried under vacuum
4. customto obtain a pale yellow solid
5. customThe above reaction mixture
6. temperaturewas cooled to 0° C
7. customthe resulting reaction
8. stirringwas stirred at 0° C. for 1 h
9. washwashed with water
10. customThe crude product was then purified by silica gel chromatography

ORD-Eintrag

ord-75fae04c41dd4972912e121f1787796b

Quelldatensatz

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09108981B2