반응 #66044

반응 방정식

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

methanol

thionyl chloride

→

title compound

수율 100.0%

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

수율 100.0%

반응 조건

후처리

1. 1
   기타was removed by evaporation
2. 2
   기타the product crystallized with diethyl ether
3. 3
   기타The diethyl ether was removed by evaporation

실험 절차

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.

출처