Water → Rivaroxaban

HRID 1054154Notes

Reaction equation

HRID 1054154 reaction equation
[O:1]=[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][C:14]3=[O:19])=[CH:9][CH:8]=2)[CH2:5][C@H:4]([CH2:20][NH:21][CH:22]=[O:23])[O:3]1.[Cl:24][C:25]1[S:29][C:28](C(Cl)=O)=[CH:27][CH:26]=1.C(OCC)(=O)C.O>O1CCCC1.[H-].[Na+].CO.C(O)(=O)C>[CH:11]1[C:10]([N:13]2[C:14](=[O:19])[CH2:15][O:16][CH2:17][CH2:18]2)=[CH:9][CH:8]=[C:7]([N:6]2[C:2](=[O:1])[O:3][C@@H:4]([CH2:20][NH:21][C:22]([C:28]3[S:29][C:25]([Cl:24])=[CH:26][CH:27]=3)=[O:23])[CH2:5]2)[CH:12]=1

Participants

9

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 5892235-Chlorothiophene-2-carbonyl ChlorideHCID 90258317N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide

Product 1

HCID 9875401Rivaroxaban

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 24758Sodium hydrideSolvent

Procedure

N-({(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl}methyl)formamide (1 g) taken in a mixture of tetrahydrofuran (10 ml) and sodium hydride (0.11 g) stirred reaction mass at 25 to 30° C. for 30 minutes. To this mixture added 5-chlorothiophene carbonyl chloride (0.86 g). Obtained reaction mass then stirred for 1 to 2 h at 25 to 30° C. After completion of reaction, added ethyl acetate and water. Separated organic layer and concentrated under reduced pressure to obtain residue. Added acetic acid and methanol to residue stirred for 30 minutes and obtained solid is filtered off. Washed solid with methanol

Workup

  1. customreaction mass at 25 to 30° C. for 30 minutes
  2. customObtained
  3. customreaction mass
  4. stirringthen stirred for 1 to 2 h at 25 to 30° C
  5. customAfter completion of reaction
  6. concentrationSeparated organic layer and concentrated under reduced pressure
  7. customto obtain residue
  8. customobtained solid
  9. filtrationis filtered off
  10. washWashed solid with methanol

Sources & evidence

ORD record
ord-abebbcedc7fe4a0b8813176101e36c6f
Source dataset
uspto-grants-2016_07
Patent number
US09394292B2

Reaction notes

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