| Identification | Back Directory | [Name]
METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE | [CAS]
89524-99-2 | [Synonyms]
Ac-Gly(PO(OMe)2-OMe
Ac-α-phosphonoglycine trimethyl ester
Trimethyl α-(Acetamido)phosphonoacetate
methyl 2-acetamido-2-(dimethoxyphosphoryl)acetate
METHYL-2-N-(ACETYLAMINO)-DIMETHYL PHOSPHONO ACETATE
methyl 2-acetylamino-2-(dimethoxyphosphinyl)acetate
Methyl alpha-(acetylamino)-alpha-(dimethoxyphosphoryl)acetate
Acetic acid, (acetylaMino)(diMethoxyphosphinyl)-, Methyl ester
Acetic acid,2-(acetylaMino)-2-(diMethoxyphosphinyl)-, Methyl ester | [Molecular Formula]
C7H14NO6P | [MDL Number]
MFCD08443722 | [MOL File]
89524-99-2.mol | [Molecular Weight]
239.16 |
| Chemical Properties | Back Directory | [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 |
| Hazard Information | Back Directory | [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 |
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