| Company Name: |
BOC Sciences |
| Tel: |
1-631-485-4226; 16314854226 |
| Email: |
info@bocsci.com |
|
| | Ganciclovir Mono-O-acetate Basic information |
| Product Name: | Ganciclovir Mono-O-acetate | | Synonyms: | 9-[[2-(Acetyloxy)-1-(hydroxymethyl)ethoxy]methyl]-2-amino-1,9-dihydro- 6H-Purin-6-on;Ganciclovir Mono-O-acetate;Gancyclovir Impurity 20;6h-purin-6-one,9-[[2-(acetyloxy)-1-(hydroxymethyl)ethoxy]methyl]-2-amino-1,9-dihydro-;[2-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]-3-hydroxypropyl] acetate;9-[[2-(Acetyloxy)-1-(hydroxymethyl)ethoxy]methyl]-2-amino-1,9-dihydro- 6H-Purin-6-one;Ganciclovir-Mono-O-acetate(Mono-O-AcetylGanciclovir);2-[(2-aMino-6-oxo-3,6-dihydro-9H-purin-9-yl)Methoxy]-3-hydroxypropyl acetate | | CAS: | 88110-89-8 | | MF: | C11H15N5O5 | | MW: | 297.27 | | EINECS: | 680-297-7 | | Product Categories: | Intermediates & Fine Chemicals;Pharmaceuticals | | Mol File: | 88110-89-8.mol |  |
| | Ganciclovir Mono-O-acetate Chemical Properties |
| Melting point | 194-197°C | | density | 1.66±0.1 g/cm3(Predicted) | | storage temp. | Keep in dark place,Inert atmosphere,2-8°C | | solubility | DMSO (Slightly), Methanol (Slightly) | | form | Solid | | pka | 9.32±0.20(Predicted) | | color | White |
| | Ganciclovir Mono-O-acetate Usage And Synthesis |
| Chemical Properties | White Solid | | Uses | Ganciclovir derivative. | | Synthesis | The general procedure for the synthesis of 2-((2-amino-6-oxo-1H-purin-9(6H)-yl)methoxy)-3-hydroxypropyl acetate from 1-acetylimidazole and 2-amino-9-(((1,3-dihydroxypropan-2- yl)oxy)methyl)-1H-purin-6(9H)-one is as follows: 500.0 g (1.96 mol, 1.0 equiv) of ganciclovir, 244.4 g (2.35 mol, 1.2 eq.) of trimethyl borate and 7.5 kg of toluene were added to the reaction vessel and heated to reflux for 5 hours. The progress of the reaction was monitored by TLC to confirm the complete reaction of the ingredients. The reaction mixture was cooled to room temperature and 396.7 g (3.93 mol, 2.0 eq.) of triethylamine was added, followed by 323.7 g (2.94 mol, 1.5 eq.) of 1-acetylimidazole, and stirred for 6 hours at room temperature. The ratio of monoacetyl ganciclovir to N,O-diacetyl ganciclovir was analyzed by HPLC to be 94:4. The reaction mixture was cooled to 0-10 °C and 2.0 kg of methanol was slowly added dropwise followed by stirring for 2 h at room temperature. The solvent was removed by concentration under reduced pressure, 3.0 kg of ethyl acetate was added, the organic layer was washed with 500 g of water and the aqueous layer was extracted with 500 g of ethyl acetate. The organic layers were combined, concentrated under reduced pressure and recrystallized by ethanol to give 440.9 g of colorless crystal product in 75.7% yield and 99.2% purity. | | References | [1] Patent: CN108383840, 2018, A. Location in patent: Paragraph 0033; 0034; 0043; 0045; 0050
[2] Patent: CN108503642, 2018, A. Location in patent: Paragraph 0028-0034; 0039; 0040; 0042-0050; 0053; 0054
[3] Patent: CN108503641, 2018, A. Location in patent: Paragraph 0030; 0031; 0033; 0034; 0040-0051; 0054; 0055
[4] Patent: CN108409739, 2018, A. Location in patent: Paragraph 0033; 0034; 0043; 0045; 0050 |
| | Ganciclovir Mono-O-acetate Preparation Products And Raw materials |
|