Diethyl Ether → HCID 10725638, compound

Triethylamine (7.40 mL, 53.1 mmol) was added slowly to a mixture of (2S,3R)-methyl 2-amino-3-hydroxybutanoate hydrochloride (3.0 g, 17.7 mmol) in dichloromethane (41 mL) at 0° C. The mixture was stirred for 15 minutes. A mixture of triphosgene (1.79 g, 6.01 mmol) in dichloromethane (15 mL) was added drop wise via addition funnel. The mixture was allowed to warm to room temperature for 14 hours. Diethyl ether (20 mL) was added, and the mixture was cooled to −78° C. for 15 minutes. The solids were filtered and the filtrate was concentrated under reduced pressure to about 10 mL. The mixture was then added to a plug of silica gel and washed slowly with ethyl acetate (˜75 mL). The filtrate was then concentrated under reduced pressure and dried under vacuum to afford (4S,5R)-methyl 5-methyl-2-oxooxazolidine-4-carboxylate. 1H NMR (500 MHz, CDCl3) δ 5.96 (s, 1H), 4.77-4.71 (m, 1H), 3.99 (d, J=5.4 Hz, 1H), 3.81 (s, 3H), 1.56 (d, J=6.3 Hz, 3H).

1. additionwas added drop
2. additionwise via addition funnel
3. temperaturethe mixture was cooled to −78° C. for 15 minutes
4. filtrationThe solids were filtered
5. concentrationthe filtrate was concentrated under reduced pressure to about 10 mL
6. additionThe mixture was then added to a plug of silica gel
7. washwashed slowly with ethyl acetate (˜75 mL)
8. concentrationThe filtrate was then concentrated under reduced pressure
9. customdried under vacuum

ORD record

ord-20b3672df80547a39991559ac9a6ae89

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09242984B2