Chemical Properties
white to off-white crystalline powder or crystals
Uses
1-Adamantaneacetic acid was used as an acylating agent in determining pharmacological characteristics of ten new analogues of bradykinin (Arg-Pro-Pro-Gly-Phe-Ser-Pro-Phe-Arg) that were modified in the N-terminal part of the molecule.
Biochem/physiol Actions
1-Adamantaneacetic acid is an inhibitor of chorismate mutase-prephenate dehydrogenase (EC 1.3.1.12) from Escherichia coli K12 (strain JP 232).
Synthesis
General procedure for synthesizing 1-adamantylacetic acid from methyl 2-(adamantan-1-yl)acetate and sodium bicarbonate: referring to the preparation of 2-adamantylacetic acid in Example 10, 2.53 g of sodium hydroxide was dissolved in 433 mL of methanol, and 1,125 mL of methanol solution containing 150 g (0.72 mol) of methyl 2-adamantylacetic acid was added, and the reaction was stirred at room temperature for 6 hours at room temperature with stirring. Upon completion of the reaction, the reaction mixture was concentrated under vacuum. To the concentrated residue was added aqueous sodium bicarbonate solution and the mixture was washed with ether. Subsequently, the aqueous layer was adjusted to pH 1 with 12N hydrochloric acid and extracted with ethyl acetate. The combined extracts were dried with anhydrous sodium sulfate. After filtration to remove the desiccant, the filtrate was concentrated in vacuum to give the target product 1-adamantaneacetic acid. Yield: 129.39 g, 93% yield.
Purification Methods
Dissolve the acid in hot NaOH, treat with charcoal, filter and acidify. Collect the solid, wash it with H2O, dry and recrystallise it from
MeOH. [Stetter et al. Chem Ber 92 1629 1959.] The acid chloride [2094-72-6] has M 168.7, m 51-54o,
and b 135-136o/1mm. LACHRYMATORY.
References
[1] Patent: US5658923, 1997, A
