تفاعل #91992

معادلة التفاعل

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

sodium carbonate

methyl iodide

→

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

المردود 98.1%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   أخرىthe 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
   أخرىformed slowly over 72 h
5. 5
   ترشيحThe precipitated solids were collected by filtration
6. 6
   غسيلwashed with water (2 L)
7. 7
   أخرىAfter air and vacuum drying

الإجراء التجريبي

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.

المصدر