L-Serine → HCID 11651229, compound

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]+.

1. customthe resultant solution was decanted from the insoluble material
2. customa white solid precipitated which
3. dissolutionredissolved
4. stirringupon stirring
5. customThe reaction vessel was sealed
6. waitleft
7. waitto stand overnight in a refrigerator
8. additionFurther diethyl ether (60 ml) was added to the cold solution
9. stirringwith stirring
10. filtrationThe resultant fine white precipitate was collected by filtration
11. washwashed with diethyl ether
12. customdried under vacuum

ORD record

ord-7c821d6194f045939a60531f9327a32c

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08518989B2