Proton sponge → (S)-2-tert-Butoxycarbonylamino-3-methoxypropionic acid benzyl ester

To a solution of the compound of Formula XII(a), (S)-2-tert-butoxycarbonylamino-3-hydroxy-propionic acid benzyl ester (1.7 g, 5.76 mmol) in dichloromethane (50 mL) was added trimethyloxonium tetrafluoroborate (1.11 g, 7.50 mmol), followed by the portion-wise addition of proton sponge (1.61 g, 7.50 mmol). After stirring for 24 hrs at RT, the solution was concentrated, and the residue was dissolved in ethyl acetate, and the solution filtered through a pad of celite. The filtrate was washed with 1 M HCl and brine. The organic layers were dried over MgSO4, filtered, and concentrated in vacuo. Silica-gel flash chromatography with 5% to 15% ethyl acetate in hexanes afforded the compound of Formula XIII(b), (S)-2-tert-butoxycarbonylamino-3-methoxy-propionic acid benzyl ester (1.24 g, 69.6%) as a colorless oil. 1H NMR (300 MHz, CDCl3): δ (ppm) 7.35-7.29 (m, 5H), 4.90-4.87 (m, 1H), 4.51 (s, 2H), 3.92-3.87 (m, 1H), 3.80-3.78 (m, 1H), 3.56 (dd, 2H), 3.42 (dd, 1H), 3.33 (s, 3H), 1.42 (s, 9H).

1. concentrationthe solution was concentrated
2. dissolutionthe residue was dissolved in ethyl acetate
3. filtrationthe solution filtered through a pad of celite
4. washThe filtrate was washed with 1 M HCl and brine
5. dry with materialThe organic layers were dried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo

ORD 기록

ord-9782e5cd3b1345a4baac6656ba3a5fd9

출처 데이터셋

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US09441012B2