Triethylamine → Methanesulfonic acid (5R)-3-(3-fluoro-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester

Temperatur

2.5 °C

A solution of iodo-alcohol 104 (25.2 g, 74.8 mmol) in methylene chloride (CH2Cl2, 150 mL) was treated with triethylamine (TEA, 15.15 g, 20.9 mL, 150 mmol, 2.0 equiv) at 25° C., and the resulting mixture was cooled to 0-5° C. before methanesulfonyl chloride (MsCl, 10.28 g, 6.95 mL, 89.7 mmol, 1.2 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 (100 mL) and CH2Cl2 (100 mL). The two layers were separated, and the aqueous layer was extracted with CH2Cl2 (100 mL). The combined organic extracts were washed with H2O (2×100 mL) and saturated aqueous NaCl (100 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-4-iodo-phenyl)-2-oxo-oxazolidin-5-ylmethyl ester 105 (30.71 g, 98.9% yield) as an off-white powder. This product was directly used in subsequent reactions without further purification. C11H11FINO5S, LCMS (EI) m/e 416 (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 (100 mL) and CH2Cl2 (100 mL)
4. customThe two layers were separated
5. extractionthe aqueous layer was extracted with CH2Cl2 (100 mL)
6. washThe combined organic extracts were washed with H2O (2×100 mL) and saturated aqueous NaCl (100 mL)
7. dry with materialdried over MgSO4
8. concentrationconcentrated in vacuo
9. customThe residue was further dried in vacuo

ORD-Eintrag

ord-cfbfb17081de4f31968f2d594ed7f1df

Quelldatensatz

uspto-grants-2014_11

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08895741B2