N-t-Boc-L-serine Allyl Ester → HCID 14683522, compound
Reaction equation
[CH2:1]([O:4][C:5](=[O:17])[C@H:6]([CH2:15][OH:16])[NH:7]C(OC(C)(C)C)=O)[CH:2]=[CH2:3].C(O)(C(F)(F)F)=O.C(Cl)Cl>CCOCC>[CH2:1]([O:4][C:5](=[O:17])[C@H:6]([CH2:15][OH:16])[NH2:7])[CH:2]=[CH2:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
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.