Реакция #51498

Уравнение реакции

ammonium hydroxide

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid

potassium carbonate

dimethyl sulfate

→

title compound

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid methyl ester

Растворители

DMF

Условия реакции

Обработка

1. 1
   workup.ADDITIONis added
2. 2
   workup.STIRRINGThe contents are stirred for 30 min
3. 3
   Температураthen cooled to 0°
4. 4
   Фильтрацияfiltered
5. 5
   ПромывкаThe solids are washed with cold water (20 mL)
6. 6
   Другоеdried under reduced pressure

Методика

(2S)-2-[(tert-butoxycarbonyl)amino]-3-(3,5-difluorophenyl)propanoic acid (I, 5.0 g, 0.017 moles, 1.0 equivalent) and potassium carbonate (2.5 g, 0.018 moles, 1.1 equivalent) and DMF (100 mL) are mixed. To this heterogeneous mixture is then added dimethyl sulfate (1.6 mL, 2.1 g, 0.017 moles, 1.0 equivalent) and the contents are then stirred at 20-25° overnight. Once the reaction is complete as measured by HPLC, ammonium hydroxide (10%, 20 mL) is added and allowed to stir for 1 hr. The contents are stirred for 30 min then cooled to 0° and filtered. The solids are washed with cold water (20 mL) and dried under reduced pressure to give the title compound.

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