1,3-Dibromopropane → (S)-4-Benzyl-3-((S)-3-(4-(2-bromopropoxy)phenyl)-3-(isoxazol-3-yl)propanoyl)oxazolidin-2-one

A mixture of 7.5 (200 mg, 0.51 mmol), 1,3-dibromopropane (1.00 mL, 10 mmol), potassium carbonate (210 mg, 1.500 mmol) and tetrabutylammonium bromide (16 mg, 0.051 mmol) in water (6.0 mL) was heated to reflux and stirred for two hours. The mixture was then cooled to room temperature and extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine and dried over magnesium sulfate. The filtrate was concentrated under reduced pressure and the residue was recrystallized with EtOAc and hexanes to obtain 48.1 (160 mg). MS ESI (pos.): m/e 514.0 (M+H).

1. temperaturewas heated
2. temperatureto reflux
3. extractionextracted with EtOAc (2×50 mL)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over magnesium sulfate
6. concentrationThe filtrate was concentrated under reduced pressure
7. customthe residue was recrystallized with EtOAc and hexanes

ORD 기록

ord-541fe07af02a436bad9f1248e23e5247

출처 데이터셋

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08003648B2