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| | 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate Basic information |
| | 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate Chemical Properties |
| Melting point | 111-112°C | | Boiling point | 459.9±34.0 °C(Predicted) | | density | 1.28±0.1 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Dichloromethane, Ether, Ethyl Acetate, Methanol | | form | Solid | | pka | 5.67±0.10(Predicted) | | color | White | | InChI | InChI=1S/C17H19NO3S/c1-22(19,20)21-16-12-18(13-16)17(14-8-4-2-5-9-14)15-10-6-3-7-11-15/h2-11,16-17H,12-13H2,1H3 | | InChIKey | MSVZMUILYMLJCF-UHFFFAOYSA-N | | SMILES | N1(C(C2=CC=CC=C2)C2=CC=CC=C2)CC(OS(C)(=O)=O)C1 | | CAS DataBase Reference | 33301-41-6(CAS DataBase Reference) |
| Safety Statements | 24/25 | | HazardClass | IRRITANT | | HS Code | 29339900 |
| | 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate Usage And Synthesis |
| Chemical Properties | White Crystalline Solid | | Uses | A proline analog and proline formation inhibitor | | Synthesis | Preparation procedure of 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate: To a reaction flask was charged 632 g (2.64 mol) of 1-benzhydrylazetidin- 3-ol, acetonitrile (1.9 L), and triethylamine (601 g, 1.5 equiv). The mixture was cooled in an ice-acetone bath (-5 °C). Methanesulfonyl chloride (436 g, 1.20 equiv) was added via a drop funnel while keeping the reaction temperature at less than5 °C. HPLC showed reaction completion after 15 min. Water (6.3 L) was added, and the reaction mixture was stirred for 2 h at room temperature and filtered. The filter cake was rinsed with water (2 x 1 L), pulled dry under vacuum, and directly subjected to the amination reaction in the next step. Yield 100%.
 | | References | [1] Patent: US2005/54697, 2005, A1. Location in patent: Page/Page column 78
[2] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 4, p. 1084 - 1088
[3] Patent: WO2011/61214, 2011, A1. Location in patent: Page/Page column 85-86
[4] Patent: US2014/288045, 2014, A1. Location in patent: Paragraph 0605
[5] Patent: WO2016/44772, 2016, A1. Location in patent: Paragraph 319 |
| | 1-(Diphenylmethyl)-3-azetidinyl methanesulfonate Preparation Products And Raw materials |
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