(R)-benzyl 2-((S)-2-oxooxazolidin-4-yl)propanoate → (R)-2-((S)-2-oxooxazolidin-4-yl)propanoic acid

To a solution of (R)-benzyl 2-((S)-2-oxooxazolidin-4-yl)propanoate (1.99 g, 7.98 mmol) in THF (18.7 mL) was added Pd/C (10% wt., Degussa; 0.425 g). The mixture was stirred under hydrogen atmosphere (balloon) at room temperature for 4 hr. The mixture was filtered through a plug of celite and rinsed several times with THF. The filtrate was concentrated under reduced pressure providing (R)-2-((S)-2-oxooxazolidin-4-yl)propanoic acid (1.17 g) as a white solid, which was directly used without further purification. MS m/z 160.0 (M+H)+; Rt-0.26 min. 1H NMR (400 Mhz, CD3OD) δ ppm 4.53-4.47 (m, 1H), 4.26 (dd, J=5.7, 9.1 Hz, 1H), 4.13 (td, J=6.0, 8.8 Hz, 1H), 2.69-2.61 (m, 1H), 1.18 (d, J=7.2 Hz, 3H).

1. filtrationThe mixture was filtered through a plug of celite
2. washrinsed several times with THF
3. concentrationThe filtrate was concentrated under reduced pressure

ORD-Eintrag

ord-6e55d54200794238ac896419a4b4da55

Quelldatensatz

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09434719B2