Реакция #91992

Уравнение реакции

(S)-3-[4-nitrophenyl]-2-tert-butoxycarbonylamino-propionic acid

sodium carbonate

methyl iodide

→

(S)-3-[4-nitrophenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester

Выход 98.1%

Растворители

DMF

Условия реакции

Обработка

1. 1
   Другоеthe excess methyl iodide and some DMF were removed under high vacuum
2. 2
   workup.ADDITIONThen, it was poured into water (2 L)
3. 3
   workup.STIRRINGstirred at room temperature as a precipitate
4. 4
   Другоеformed slowly over 72 h
5. 5
   ФильтрацияThe precipitated solids were collected by filtration
6. 6
   Промывкаwashed with water (2 L)
7. 7
   ДругоеAfter air and vacuum drying

Методика

To a suspension of (S)-3-[4-nitrophenyl]-2-tert-butoxycarbonylamino-propionic acid (70.2 g, 226.2 mmol) and sodium carbonate (95 g, 1.13 mole) in DMF (500 mL) was added methyl iodide (70.4 mL, 1.13 mole) at room temperature. The suspension was stirred for 15 h at room temperature at which time TLC analysis of the mixture indicated the absence of starting material and the excess methyl iodide and some DMF were removed under high vacuum. Then, it was poured into water (2 L) and stirred at room temperature as a precipitate formed slowly over 72 h. The precipitated solids were collected by filtration and washed with water (2 L). After air and vacuum drying, 72 g (98% yield) of (S)-3-[4-nitrophenyl]-2-tert-butoxycarbonylamino-propionic acid methyl ester was isolated as a light yellow solid (mp 95-96° C.). ES(+)-HRMS m/e calcd. for C15H20N2O6 (M+H)+ 325.1400, obsd. 325.1404.

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