| Identification | Back Directory | [Name]
2-(3,5-bis(trifluoroMethyl)phenyl)-2-Methyl propanoic acid | [CAS]
289686-70-0 | [Synonyms]
Netupitant SM1
Netupitant int4
α,α-DiMethyl-3,5-bis(trifluoroMethyl)benzeneaceticAcid
2-(3,5-bis(trifluoroMethyl)phenyl)-2-Methyl propanoic acid
Benzeneacetic acid, α,α-dimethyl-3,5-bis(trifluoromethyl)- | [EINECS(EC#)]
-0 | [Molecular Formula]
C12H10F6O2 | [MDL Number]
MFCD09032572 | [MOL File]
289686-70-0.mol | [Molecular Weight]
300.197 |
| Chemical Properties | Back Directory | [Melting point ]
105.5-107℃ | [Boiling point ]
232.5±35.0 °C(Predicted) | [density ]
1.378±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,Room Temperature | [pka]
4.06±0.14(Predicted) | [Appearance]
White to off-white Solid | [InChI]
InChI=1S/C12H10F6O2/c1-10(2,9(19)20)6-3-7(11(13,14)15)5-8(4-6)12(16,17)18/h3-5H,1-2H3,(H,19,20) | [InChIKey]
ORLKRFYFNMCQIG-UHFFFAOYSA-N | [SMILES]
C(O)(=O)C(C1=CC(C(F)(F)F)=CC(C(F)(F)F)=C1)(C)C |
| Hazard Information | Back Directory | [Uses]
2-?(3,?5-?Bis(trifluoromethyl)?phenyl)?-?2-?methylpropanoic Acid is a reagent used in the synthesis of NK1/NK3 receptor antagonists used in the treatment of depression. | [Synthesis]
The general procedure for the synthesis of 2-(3,5-bis-trifluoromethyl-phenyl)-2-methylpropanoic acid using nerapitant impurity 20 as a starting material was as follows: lithium hydroxide monohydrate (2.13 g, 50.6 mmol) was added to α,α-dimethyl-3,5-bis(trifluoromethyl)benzeneacetic acid methyl ester (5.3 g, 16.88 mmol) in a methanol (60 mL), water (20 mL) and tetrahydrofuran (20 mL) in a suspension. The mixture was degassed and the reaction was stirred at room temperature for 3 days. Upon completion of the reaction, the solvent was removed by distillation under reduced pressure. The residue was suspended in 1 M hydrochloric acid and extracted with ethyl acetate. The organic phases were combined and dried over anhydrous magnesium sulfate, followed by evaporation of the solvent under reduced pressure to afford the target product 2-(3,5-bis-trifluoromethyl-phenyl)-2-methylpropanoic acid as a colorless solid (5.05 g, 100% yield). The structure of the product was confirmed by 1H NMR (400 MHz, CDCl3): δ 7.84 (2H, s), 7.80 (1H, s), 1.68 (6H, s). | [References]
[1] Patent: US2003/225059, 2003, A1. Location in patent: Page 22
[2] Patent: US2003/236250, 2003, A1. Location in patent: Page 18
[3] Patent: CN107721815, 2018, A. Location in patent: Paragraph 0039; 0041; 0051; 0053; 0055; 0065; 0069; 0079
[4] Bioorganic and medicinal chemistry letters, 2002, vol. 12, # 13, p. 1755 - 1758
[5] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 19, p. 5310 - 5315 |
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