Methanol → (R)-Methyl 2-aminopent-4-enoate hydrochloride

Reaktionsgleichung

[NH2:1][C@H:2]([CH2:6][CH:7]=[CH2:8])[C:3]([OH:5])=[O:4].S(Cl)([Cl:11])=O.[CH3:13]O>>[ClH:11].[NH2:1][C@H:2]([CH2:6][CH:7]=[CH2:8])[C:3]([O:5][CH3:13])=[O:4]

Komponenten

Edukt 3

HCID 887Methanol

HCID 24386Thionyl Chloride

HCID 6992334(+)-Allylglycine

Produkt 1

HCID 11446532(R)-Methyl 2-aminopent-4-enoate hydrochlorideAusbeute 100 %

Versuchsvorschrift

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.