L-Serine → HCID 11651229, compound

Participants

Reaction Steps

L-Serine (10.5 g, 0.10 mol) was added with stifling to trifluoroacetic acid (70 ml) and the resultant solution was decanted from the insoluble material. Butyryl chloride (13.5 ml, 0.123 mol) was then added to the solution and the mixture was stirred for 1 h at room temperature. Upon the addition of diethyl ether (20 ml), a white solid precipitated which redissolved upon stirring. The reaction vessel was sealed and left to stand overnight in a refrigerator. Further diethyl ether (60 ml) was added to the cold solution with stirring. The resultant fine white precipitate was collected by filtration, washed with diethyl ether, and dried under vacuum to afford 13.4 g (60.0 mmol, 63%) of 2020371, m.p. 165-168° C. (dec.). 1H NMR (300 MHz, d6-DMSO) δ 0.80 (t, J 7 Hz, 3H), 1.46 (m, 2H), 2.24 (m, 2H), 4.21 (br s, 1H), 4.38 (m, 2H), 8.75 (br s, 3H). 13C NMR (75.5 MHz, d6-DMSO) δ 13.5, 18.1, 35.1, 57.7, 62.1, 168.3, 173.0. m/z 176.1 [M+H]+.

Provenance & Evidence