Reaction #66044

Reaction equation

(2R)-2-amino-4-pentenoic acid

methanol

thionyl chloride

→

title compound

Yield 100.0%

Methyl (2R)-2-amino-4-pentenoate hydrochloride

Yield 100.0%

Conditions

Workup

1. 1
   Otherwas removed by evaporation
2. 2
   Otherthe product crystallized with diethyl ether
3. 3
   OtherThe diethyl ether was removed by evaporation

Procedure

To a suspension of (2R)-2-amino-4-pentenoic acid (200 mg, 1.74 mmol) in methanol (6 mL) at 0° C. was added dropwise thionyl chloride (1 mL). The resulting solution was allowed to stir for 16 h before the solvent was removed by evaporation and the product crystallized with diethyl ether. The diethyl ether was removed by evaporation to yield the title compound (287 mg, 1.74 mmol, 100%) as a white solid which had spectral data in agreement with that reported.123 Mp 135-140° C. 1H NMR (CDCl3, 300 MHz): δ 8.70 (bs, 3H, NH3′); 5.89 (m, 1H, H4); 5.32 (d, J=17.3 Hz, 1H, H5a); 5.24 (d, J=10.1 Hz, 1H, H5b); 4.31 (m, 1H, H2); 3.81 (s, 3H, OCH3); 2.87 (t, J=6.3 Hz, 2H, H3). Mass Spectrum (ES, +ve) m/z 130 (100%) [M+]. HRMS calcd for C6H12NO2 130.0868, found 130.0870.

Source