Reaktion #364971

Reaktionsgleichung

(S)-(−)-N-[[2-oxo-3-[4-(4-piperidinyl)phenyl]-5-oxazolidinyl]methyl]acetamide

(S)-(−)-N-[[2-Oxo-3-[4-(4-piperidinyl)phenyl]-5-oxazolidinyl]methyl]acetamide

triethylamine

benzyloxyacetyl chloride

→

title compound

(S)-(−)-N-[[3-[4-[1-[(Benzyloxy)acetyl]-4-piperidinyl]phenyl]-2-oxo-5-oxazolidinyl]methyl]acetamide

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenThe reaction mixture is then washed with water (2×10 mL), saturated aqueous sodium bicarbonate (10 mL) and saline (10 mL)
2. 2
   Trocknendried over anhydrous sodium sulfate
3. 3
   Einengenconcentrated under reduced pressure
4. 4
   Sonstigeto give the crude product which
5. 5
   Sonstigeis chromatographed on silica gel (230-400 mesh, 45 g)
6. 6
   Wascheneluting with a gradient of methanol/methylene chloride (11/99-2/98)

Vorschrift

A mixture of (S)-(−)-N-[[2-oxo-3-[4-(4-piperidinyl)phenyl]-5-oxazolidinyl]methyl]acetamide (EXAMPLE 17, 300 mg) and triethylamine (0.20 mL) in dry methylene chloride (19 mL) at 0° C. under N2 is treated with benzyloxyacetyl chloride (0.18 mL), and the resulting solution is stirred at 0° C. for one hour and at ambient temperature for one hour. The reaction mixture is then washed with water (2×10 mL), saturated aqueous sodium bicarbonate (10 mL) and saline (10 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to give the crude product which is chromatographed on silica gel (230-400 mesh, 45 g), eluting with a gradient of methanol/methylene chloride (11/99-2/98). Pooling and concentration of those fractions with an Rf=0.28 by TLC (methanol/chloroform, 5/95) gives the title compound, NMR (CDCl3, 400 MHz) 7.45, 7.35, 7.18, 6.26, 4.75, 4.63, 4.22, 4.04, 3.78, 3.70, 3.60, 3.09, 2.70, 2.02, 1.85, 1.60δ.

Quelle