Methanesulfonyl chloride → (5R)-3-(3-Fluorophenyl)-5-[[(methylsulfonyl)oxy]methyl]-2-oxazolidinone

온도

2.5 °C

A solution of alcohol 103 (6.33 g, 30.0 mmol) in CH2Cl2 (60 mL) was treated with TEA (6.07 g, 8.36 mL, 60 mmol, 2.0 equiv) at 25° C., and the resulting mixture was cooled to 0-5° C. before MsCl (3.78 g, 2.55 mL, 33.0 mmol, 1.1 equiv) was dropwise introduced into the reaction mixture at 0-5° C. under N2. The resulting reaction mixture was subsequently stirred at 0-5° C. for 1 h under N2. When TLC and HPLC/MS showed the reaction was complete, the reaction mixture was quenched with H2O (40 mL) and CH2Cl2 (40 mL). The two layers were separated, and the aqueous layer was extracted with CH2Cl2 (40 mL). The combined organic extracts were washed with H2O (2×40 mL) and saturated aqueous NaCl (40 mL), dried over MgSO4, and concentrated in vacuo. The residue was further dried in vacuo to afford the desired (5R)-methanesulfonic acid 3-(3-fluoro-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester 109 (7.69 g, 88.7% yield) as an off-white powder. This product was directly used in subsequent reactions without further purification. C11H12FNO5S, LCMS (EI) m/e 290 (M++H).

1. additionwas dropwise introduced into the reaction mixture at 0-5° C. under N2
2. customThe resulting reaction mixture
3. customthe reaction mixture was quenched with H2O (40 mL) and CH2Cl2 (40 mL)
4. customThe two layers were separated
5. extractionthe aqueous layer was extracted with CH2Cl2 (40 mL)
6. washThe combined organic extracts were washed with H2O (2×40 mL) and saturated aqueous NaCl (40 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo
9. customThe residue was further dried in vacuo

ORD 기록

ord-3572c9edc26b4d179c3fda365aa86199

출처 데이터셋

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08895741B2