(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one.HCl Chemical Properties

Melting point:

>276°C (dec.)

storage temp. 

Sealed in dry,Room Temperature

solubility 

DMSO (Slightly), Water (Slightly)

form 

Solid

pka

8.96[at 20 ℃]

color 

White to Off-White

Water Solubility 

184.9g/L at 20℃

InChI

InChI=1/C14H17N3O4.ClH/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;1H/t12-;/s3

InChIKey

ITMQDYQHNKXERQ-ZLBVLXFENA-N

SMILES

O=C1O[C@@H](CN)CN1C1C=CC(N2CCOCC2=O)=CC=1.Cl |&1:3,r|

LogP

-0.1 at 25℃

(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one.HCl Usage And Synthesis

Uses

Rivaroxaban intermediate.

Flammability and Explosibility

Non flammable

Synthesis

The general procedure for the synthesis of (S)-4-(4-(5-(aminomethyl)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione from 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione was carried out in the following steps: in a four-necked round-bottomed flask. Methanol (2900 mL), 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione (290 g), and 40% aqueous methylamine solution (265 g) were added. The reaction mixture was stirred at 25 to 30 °C for 1 hour, then heated to 60 to 65 °C and maintained at that temperature for 4 hours. Upon completion of the reaction, the mixture was cooled to 25 to 30 °C, concentrated hydrochloric acid (290 mL, adjusted pH to 1-2) was added and stirring was continued for 30 minutes. The resulting solid was collected by filtration and washed with cold methanol (290 mL). The yield was 92.0%.

References

[1] Patent: WO2014/102820, 2014, A2. Location in patent: Paragraph 059
[2] Patent: CN105085371, 2017, B. Location in patent: Paragraph 0102-0104
[3] Patent: CN105085431, 2017, B. Location in patent: Paragraph 0093; 0094; 0095; 0096; 0097; 0098; 0099
[4] Patent: WO2012/35057, 2012, A2. Location in patent: Page/Page column 29
[5] Patent: WO2013/121436, 2013, A2. Location in patent: Page/Page column 27

(S)-4-(4-(5-(Aminomethyl)-2-oxooxazolidin-3-yl)phenyl)morpholin-3-one.HCl(898543-06-1)Related Product Information

• Rivaroxaban iMpurity 8
• Acetic acid, 2-chloro-2-[2-(4-methoxyphenyl)hydrazinylidene], ethyl ester
• (R)-3-Piperidinamine dihydrochloride
• (R)-3-(Boc-Amino)piperidine
• 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
• 5-CHLOROTHIOPHENE-2-CARBONYL CHLORIDE
• Ethyl (R)-(-)-4-cyano-3-hydroxybutyate
• 3-MORPHOLINONE, 4-[4-[(5S)-5-(AMINOMETHYL)-2-OXO-3-OXAZOLIDINYL]PHENYL]-
• 4-(4-AMINOPHENYL)MORPHOLIN-3-ONE
• 5-Chloro-2-thiophenecarboxylic Acid
• m-(Trifluoromethyl)phenylacetic acid
• (S)-(+)-Epichlorohydrin