3-MORPHOLINONE, 4-[4-[(5S)-5-(AMINOMETHYL)-2-OXO-3-OXAZOLIDINYL]PHENYL]- Chemical Properties

Melting point:

148.3-149.8 °C

Boiling point:

580.4±45.0 °C(Predicted)

Density 

1.348±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

8.96±0.29(Predicted)

InChI

InChI=1S/C14H17N3O4/c15-7-12-8-17(14(19)21-12)11-3-1-10(2-4-11)16-5-6-20-9-13(16)18/h1-4,12H,5-9,15H2/t12-/m0/s1

InChIKey

DEXXSYVEWAYIGZ-LBPRGKRZSA-N

SMILES

N1(C2=CC=C(N3C[C@H](CN)OC3=O)C=C2)CCOCC1=O

3-MORPHOLINONE, 4-[4-[(5S)-5-(AMINOMETHYL)-2-OXO-3-OXAZOLIDINYL]PHENYL]- Usage And Synthesis

Chemical Properties

White Solid

Uses

Rivaroxaban intermediate.

Uses

A metabolite of Rivaroxaban (R538000).

Synthesis

S1, phthalimide potassium salt (73.4 g, 0.39 mol) was added to a solution of (S)-4-chloro-3-hydroxybutanenitrile (39.5 g, 0.33 mol) in DMF (330 ml), and heated to 70 ?? C to react for 4h, the reaction solution was poured into water (440 ml), stirred for 10min, a white solid precipitated, pumped filter, the filter cake was dried under reduced pressure to give a White solid (73.6 g, 97.0%); mp 137-140??C, [??]D25-21.8?? (c1, CHCl3). S2, (S)-4-(1,3-dioxoisoindol-2-yl)-3-hydroxybutanenitrile (63.4 g, 0.28 mol) obtained from step S1 was added to chloroform (330 ml), and 30% hydrogen peroxide (122 ml, 3.95 mol), tetrabutylammonium bromide (17.7 g, 55 mmol) and 20% sodium hydroxide ( 110 ml, 3.36 mol) solution, added, raised to room temperature, stirred the reaction for 2h, added chloroform (110 ml) partition, the organic phase was washed with saturated sodium chloride solution (220 ml ?? 3), dried with anhydrous sodium sulfate, filtration, filtrate was concentrated under reduced pressure to obtain a white solid 4-[4-[(5S)-5-(aminomethyl)-2-carbonyloxy-3-azolidinyl]phenyl]-3-morphine morpholinone (65.6 g, 95.8%)

3-MORPHOLINONE, 4-[4-[(5S)-5-(AMINOMETHYL)-2-OXO-3-OXAZOLIDINYL]PHENYL]-(446292-10-0)Related Product Information

• Rivaroxaban iMpurity 8
• 3-Morpholinone, 4-(2,4-diaMinophenyl)-
• (R)-5-chloro-N-(4-(3-oxomorpholino)phenyl)-N- ((2-oxooxazolidin-5-yl)methyl)thiophene-2-carboxamide
• Benzoic acid, 2-[[[[(5S)-2-oxo-3-[4-(3-oxo-4-Morpholinyl)phenyl]-5-oxazolidinyl]Methyl]aMino]carbonyl]-
• 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-
• Rivaroxaban
• POLYSTYRENE IODOSOACETATE
• 1,2-Cyclohexanedione
• 4-(4-NITROPHENYL)MORPHOLIN-3-ONE
• (S)-(+)-Glycidyl Phthalimide
• 4-[4-(N-(3-chloro-(2R)-2-hydroxy-1-propyl)aMino)phenyl]Morpholin-3-one
• (S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one.HCl
• 5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE
• Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
• 5-Chloro-2-thiophenecarboxylic Acid
• m-(Trifluoromethyl)phenylacetic acid
• 2-[(2R)-2-Hydroxy-3-[[4-(3-oxo-4-Morpho linyl)phenyl]aMino]propyl]-1H-isoindole-1 ,3(2H)-dione
• (S)-(+)-Epichlorohydrin