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| | METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE Basic information |
| Product Name: | METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE | | Synonyms: | methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate;Acetic acid, (acetylaMino)(diMethoxyphosphinyl)-, Methyl ester;METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE;Methyl alpha-(acetylamino)-alpha-(dimethoxyphosphoryl)acetate;Acetic acid,2-(acetylaMino)-2-(diMethoxyphosphinyl)-, Methyl ester;Ac-Gly(PO(OMe)2-OMe;Ac-α-phosphonoglycine trimethyl ester;Trimethyl α-(Acetamido)phosphonoacetate | | CAS: | 89524-99-2 | | MF: | C7H14NO6P | | MW: | 239.16 | | EINECS: | | | Product Categories: | | | Mol File: | 89524-99-2.mol |  |
| | METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE Chemical Properties |
| Melting point | 88.0-88.5℃ | | Boiling point | 385.3±32.0 °C(Predicted) | | density | 1.253±0.06 g/cm3(Predicted) | | storage temp. | Sealed in dry,Room Temperature | | solubility | Chloroform (Slightly), Methanol (Slightly) | | form | Solid | | pka | 13.20±0.46(Predicted) | | color | White to Off-White | | InChI | InChI=1S/C7H14NO6P/c1-5(9)8-6(7(10)12-2)15(11,13-3)14-4/h6H,1-4H3,(H,8,9) | | InChIKey | MXNIODZSMNMILW-UHFFFAOYSA-N | | SMILES | C(OC)(=O)C(NC(C)=O)P(OC)(OC)=O |
| HazardClass | IRRITANT | | HS Code | 2915390090 |
| | METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE Usage And Synthesis |
| Uses | Trimethyl α-(Acetamido)phosphonoacetate can be prepared to use as HDAC inhibitor to treat cell proliferative diseases, autoimmune diseases, inflammation, neurodegenerative diseases or viral diseases. | | Synthesis | GENERAL STEPS: Compound C152 (12.65 g, 38.2 mmol) and acetic anhydride (9.02 mL, 95.5 mmol) were dissolved in methanol (100 mL), and the mixed solution was transferred to a Parr autoclave. 10% Pd/C catalyst (0.640 g) was added and the hydrogenation reaction was carried out at 45 psi hydrogen pressure for 3 hours. Upon completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to give an oil. The oil was placed in a depressurized environment and reduced pressure was applied to solidify it. The resulting white solid was dissolved in a small amount of ethyl acetate and pentane was slowly added with vigorous stirring until a precipitate began to form. The precipitate was separated by filtration to give methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate (C153) as a white powder in 87% yield. Mass spectrometry (chemical ionization, CI) analysis showed a molecular ion peak (M+H)+ m/z of 240 for C7H14NO6P. | | References | [1] Organic and Biomolecular Chemistry, 2018, vol. 16, # 8, p. 1277 - 1286
[2] Synthesis, 1984, # 1, p. 53 - 60
[3] Organic Syntheses, 2011, vol. 88, p. 152 - 161
[4] Tetrahedron, 2007, vol. 63, # 51, p. 12740 - 12746
[5] Patent: WO2004/39815, 2004, A2. Location in patent: Page 52 - 53 |
| | METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE Preparation Products And Raw materials |
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