Methyl N-benzyloxycarbonylglycinate → HCID 90412288, compound

Temperature

-70 °C

A solution of lithium bis(trimethylsilyl)amide (44.8 ml, 1M solution) in anhydrous THF (50 ml) was cooled to −70° C. under argon in a dry flask with stirring. To the solution was added Cbz glycine methyl ester (10.0 g) in THF (20 mL) dropwise while maintaining the reaction temperature at −70° C. After 30 min stirring at −70° C., a solution of the (E)-tetradec-2-enoyl chloride (12.1 g) in THF (10 mL) was added slowly at −70° C. The reaction mixture was stirred at −70° C. for 1 hr and then allowed to warm up to 0° C. The reaction was quenched with aqueous citric acid solution (5%, 300 ml) and warmed up to room temperature. The crude product was extracted with ethyl acetate (500 ml). The ethyl acetate phase was washed with DI water twice and dried with sodium sulfate. The solvent was removed under vacuum to yield oily residue, which was purified by silica gel column chromatography. Pure product was obtained after column purification as a clear oil (12.8 g, 66.2% yield). Proton NMR(CDCl3) δ 0.88 (t, 3H), 1.26 (m, 16H), 1.43 (m, 2H), 2.22 (m, 2H), 3.67 (s, 3H), 4.53 (s, 2H), 5.24 (s, 2H), 6.94 (d, 1H), 7.05 (td, 1H). 7.36 (m, 5H).

1. stirringAfter 30 min stirring at −70° C.
2. stirringThe reaction mixture was stirred at −70° C. for 1 hr
3. temperatureto warm up to 0° C
4. customThe reaction was quenched with aqueous citric acid solution (5%, 300 ml)
5. temperaturewarmed up to room temperature
6. extractionThe crude product was extracted with ethyl acetate (500 ml)
7. washThe ethyl acetate phase was washed with DI water twice
8. dry with materialdried with sodium sulfate
9. customThe solvent was removed under vacuum
10. customto yield oily residue, which
11. customwas purified by silica gel column chromatography
12. customPure product was obtained

ORD record

ord-d54fcc89afef494ca4593b2a3a7575f8

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09403760B2