N-t-Boc-L-serine Allyl Ester → HCID 14683522, compound

Temperature

0 °C

N-tert-butoxycarbonyl-L-serine allyl ester (27.2 g) was placed in a 500 ml r. b. flask and cooled to 0° C. To this yellow oil, 50% TFA/CH2Cl2 (100 ml) was added under positive N2 pressure. The reaction mixture was stirred at 0° C. (30 min), warmed to room temperature, and stirred for 2 h. TFA and CH2Cl2 were removed by rotoevaporation to yield a yellow oil. The yellow oil was dissolved in ether (200 ml). After 3 h at 4° C., the product completely precipitated. The precipitated product was collected by filtration and washed with ether (50 ml) and hexane (20 ml). The white precipitate was dried in a vacuum oven overnight. Dry L-serine allyl ester (3) was obtained (15.6 g, 100% yield). TLC in CH2Cl2/CH3OH/H2O (65:25:4) showed a pure product (Rf=0.58). FTIR: (thin film, cm−1) 2994.54, 2960.64, 2891.49, 1747.28, 1674.06, 1201.52, 11.45.92. 1H NMR (300 MHz, CDCl3, δ ppm): 5.86 (1H, m), 5.30 (2H, m), 4.59 (2H, d, J=6.43 Hz), 4.09 (2H, m), 3.77 (1H, m). FAB-MS [M+H+] calcd for C6H11NO3 146.2, found 146.0.

1. temperaturewarmed to room temperature
2. stirringstirred for 2 h
3. customTFA and CH2Cl2 were removed by rotoevaporation
4. customto yield a yellow oil
5. waitAfter 3 h at 4° C.
6. customthe product completely precipitated
7. filtrationThe precipitated product was collected by filtration
8. washwashed with ether (50 ml) and hexane (20 ml)
9. customThe white precipitate was dried in a vacuum oven overnight

ORD record

ord-d904a649d6f4472e86d7952175fcc0e6

Source dataset

uspto-grants-2004_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06829540B1