|
|
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).