L-Serine → HCID 56621340, compound

Participants

Reaction Steps

L-Serine (5.25 g, 50 mmol) was added with stirring to trifluoroacetic acid (35 ml) and the resultant was decanted from the insoluble material. Propionyl chloride (5.66 ml, 64.0 mmol) was then added to the solution and the mixture was stirred for 1 h at room temperature. Upon the addition of diethyl ether (6 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 (30 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 6.43 g (32.5 mmol, 65%) of 2020370, m.p. 148-150° C. (dec.). 1H NMR (300 MHz, d6-DMSO) δ 0.96 (t, J 7 Hz, 3H), 2.29 (m, 2H), 4.21 (br s, 1H), 4.39 (m, 2H), 8.75 (br s, 3H). 13C NMR (75.5 MHz, d6-DMSO) δ 8.7, 27.2, 52.0, 61.3, 168.9, 174.0. m/z 162.1 [M+H]+.

Provenance & Evidence