2-Adamantone-5-carboxylic acid Chemical Properties

Melting point:

169.5-171.0 °C(Solv: ethyl ether (60-29-7))

Boiling point:

367.6±35.0 °C(Predicted)

Density 

1.358±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

4.45±0.20(Predicted)

Appearance

Off-white to light yellow Solid

InChI

InChI=1S/C11H14O3/c12-9-7-1-6-2-8(9)5-11(3-6,4-7)10(13)14/h6-8H,1-5H2,(H,13,14)

InChIKey

VFNJWHFPIRNNRQ-UHFFFAOYSA-N

SMILES

C12(C(O)=O)CC3CC(CC(C3=O)C1)C2

Safety Information

HazardClass 

IRRITANT

HS Code 

2916399090

2-Adamantone-5-carboxylic acid Usage And Synthesis

Uses

2-Adamantanone-5-carboxylic Acid is a reactant used in the synthesis of potent inhibitors targeting the drug-resistant mutant of Influenze A. Starting material for Saxagliptin impurities.

Synthesis

General procedure for the synthesis of 2-adamantanone-5-carboxylic acid from methyl 5-formate-2-adamantanone: To a mixture of 1.92 g (9.22 mmol) of methyl 5-formate-2-adamantanone (for preparation, see US20050245534) in THF (9 mL) and methanol (3 mL), an aqueous solution of 3N sodium hydroxide (6.15 mL. 18.4 mmol). The reaction mixture was stirred at room temperature for 16 hours. Upon completion of the reaction, methanol and THF were removed by concentration. the residue was cooled in an ice bath and the pH was adjusted slowly by addition of 6N aqueous HCl solution to about 1. After continued stirring for 30 min, the precipitate was collected by filtration, washed with water and partially dried over a filter. The resulting solid was dissolved in dichloromethane (400 mL) and dried by adding anhydrous sodium sulfate. After filtration, the filtrate was concentrated and dried under vacuum to give 1.50 g (84% yield) of 2-adamantanone-5-carboxylic acid as a white solid.HPLC analysis (Condition B): retention time 1.61 min.LCMS analysis (Condition B): m/z 193.3 [M+H]+.

References

[1] Patent: WO2012/125886, 2012, A1. Location in patent: Page/Page column 93
[2] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 1, p. 67 - 73
[3] Patent: WO2009/156092, 2009, A2. Location in patent: Page/Page column 49

2-Adamantone-5-carboxylic acid(56674-87-4)Related Product Information

• Ethyl 2-(Chlorosulfonyl)acetate
• Benzoic acid
• Amantadine
• 2-Adamantanone
• 1-Adamantanecarboxylic acid
• Adamantane
• Rimantadine hydrochloride
• 5-Hydroxyadamantan-2-one
• 1-Adamantyl Methacrylate
• 1-Adamantylacrylate
• 5-CHLORO-2-ADAMANTANONE
• 1,3,5-ADAMANTANETRIOL
• 1,3-Adamantanediol monoacrylate
• 1-(Methoxyacetylamino) Adamantane (MAAA)
• 1-BROMO-3-METHYLADAMANTANE
• N,N'-(5,7-dimethyl adamantane-1,3-diyl) diacetamide
• 1-(Hydroxyacetylamino) Adamantane (HAAA)
• 1-METHYLADAMANTANE