ChemicalBook CAS DataBase List (S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine synthesis

6synthesis methods

Product Name:(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine
CAS Number:168828-90-8
Molecular formula:C14H18FN3O3
Molecular Weight:295.31

165800-03-3 Synthesis

165800-03-3
751 suppliers
$5.00/100mg

(S)-N-[[3-[3-Fluoro-4-(4-morpholinyl)phenyl]-2-oxo-5-oxazolidinyl]methyl]amine

168828-90-8
207 suppliers
$7.00/100mg

Yield:168828-90-8 99%

Reaction Conditions:

with hydrogenchloride in methanol;Reflux;

Steps:

(S)-5-(aminomethyl)-3-(3-fluoro-4-morpholinophenyl)oxazolidin-2-one, DP-60

50 mg of linezolid were dissolved in MeOH (1 mL), then conc. HCl (1 mL) was added and the reaction was heated to reflux for ON. Solvent was evaporated to dryness under vacuum, and then the product was purified by reverse phase column chromatography on prep-HPLC using gradient of (water/acetonitrile/ 0.1 %TFA). Those fractions containing pure product were pooled and lyophilized to give the pure product yellow solid, 99% yield. RP-HPLC (C18): 2 to 50% (ACN/ Water/ 0.1%TFA) in 30 min, t_R = 9.391 min, purity of 95%; ¹H NMR (399 MHz, Acetone-d6) δ 7.54 (dd, J = 15.0, 2.6 Hz, 1H), 7.20 (ddd, J = 8.9, 2.6, 1.1 Hz, 1H), 7.14 - 6.95 (m, 1H), 5.25 (q, J = 8.9, 8.5 Hz, 1H), 4.44 - 4.23 (m, 2H), 4.09 (dd, J = 9.4, 6.1 Hz, 1H), 3.82 - 3.72 (m, 4H), 3.08 - 2.94 (m, 4H);¹⁹F NMR (376 MHz, Acetone) δ -122.71; LCMS(ESI) C₁₄H₁₈FN₃O₃, [M+H]⁺: m/z calcd; 296.1, found; 296.1.

References:

Spaulding, Andrew;Takrouri, Khuloud;Mahalingam, Pornachandran;Cleary, Dillon C.;Cooper, Harold D.;Zucchi, Paola;Tear, Westley;Koleva, Bilyana;Beuning, Penny J.;Hirsch, Elizabeth B.;Aggen, James B. [Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,# 23,p. 5310 - 5321] Location in patent:supporting information