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| | 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]- Basic information | | Uses |
| | 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]- Chemical Properties |
| Melting point | 213-215°C | | Boiling point | 702.9±55.0 °C(Predicted) | | density | 1.465±0.06 g/cm3(Predicted) | | storage temp. | Inert atmosphere,Room Temperature | | solubility | Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 0.99±0.20(Predicted) | | color | White to Off-White | | Water Solubility | 12mg/L at 20℃ | | Major Application | pharmaceutical (small molecule) | | InChI | InChI=1S/C22H19N3O6/c26-19-13-30-10-9-23(19)14-5-7-15(8-6-14)24-11-16(31-22(24)29)12-25-20(27)17-3-1-2-4-18(17)21(25)28/h1-8,16H,9-13H2/t16-/m1/s1 | | InChIKey | KUQNYAUTIWQAKY-MRXNPFEDSA-N | | SMILES | C1(=O)C2=C(C=CC=C2)C(=O)N1C[C@@H]1OC(=O)N(C2=CC=C(N3CCOCC3=O)C=C2)C1 | | LogP | -0.2 at 25℃ |
| WGK Germany | WGK 2 | | Storage Class | 11 - Combustible Solids | | Hazard Classifications | Aquatic Chronic 2 |
| | 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]- Usage And Synthesis |
| Uses | 1H-isoindole-1,3(2H)-dione, 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]- is an important intermediate for the synthesis of rivaroxaban, which is an anticoagulant and the first orally active direct factor Xa inhibitor.
| | Chemical Properties | White Solid | | Uses | Rivaroxaban intermediate. | | Flammability and Explosibility | Non flammable | | Synthesis | The general procedure for the synthesis of 2-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-1H-isoindole-1,3(2H)-dione from 4-(3-oxomorpholinyl)phenyl isocyanate and (S)-2-(ethoxylen-2-ylmethyl)isoindoline-1,3-dione was as follows: the (S)- 2-(oxiran-2-ylmethyl)isoindoline-1,3-dione (4.56 g, 22.46 mmol, 1.3 eq.) and 4-(4-isocyanatophenyl)morpholin-3-one (3.77 g, 17.29 mmol) were dissolved in isoamyl acetate (70 mL), respectively. The reaction mixture was heated to 120 °C, followed by the addition of magnesium chloride (0.12 g, 1.28 mmol). After the reaction lasted for 4 h, a white solid product (6.97 g, 95.5% yield) was obtained by filtration. The product was confirmed by mass spectrometry by ESI-MS (m/z): 422 (M + H), 444 (M + Na); 1H NMR (400 MHz, CDCl3) δ: 3.74 (m, 2H), 3.94 (m, 4H), 4.10 (m, 2H), 4.32 (s, 2H), 4.98 (m, 1H), 7.34 (d, 2H), and 7.56 (d, 2H), 7.75 (m, 2H), 7.88 (m, 2H) were characterized by NMR; HPLC purity was 98.82%. | | References | [1] Patent: EP2837628, 2015, A1. Location in patent: Paragraph 0029
[2] Patent: US2015/38704, 2015, A1. Location in patent: Paragraph 0048-0051 |
| | 1H-ISOINDOLE-1,3(2H)-DIONE, 2-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]- Preparation Products And Raw materials |
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