wt/vol

 

wt/vol

MW

moles

density

equivs.

yield

I

1.507 g

133.10

0.0113

 

1.0

 

II

1.80 mL

118.97

0.0247

1.631

2.2

 

III

25 mL

-

-

 

 

 

IV

2.204 g

197.62

0.0112

 

 

(99%)

 

Procedure:  150 mL 1-neck flask, stirbar, septum, N2 inlet

                  Prepared a suspension of 1.507 g of L-aspartic acid (I) in 25 mL of absolute MeOH.  Stirred; cooled to 0 C.  Carefully added 1.80 mL of SOCl2 dropwise.  The reaction mixture was then warmed to 40 C.  After 3.5 h, the reaction mixture was then cooled to rt.  The solvent was removed by rotary evaporation to afford the product as a white solid. 

 

1H NMR (CDCl3, 400 MHz) d 8.76 (br, NH3), 4.63 (br, H2), 3.86 (s, CO2CH3), 3.76 (s, CO2CH3), 3.32 (br, H3).