ORGANIC SPECTROSCOPY INTERNATIONAL: Arterolane maleate

Arterolane

cas 664338-39-0, UNII-3N1TN351VB, OZ277, RBX-11160, NCGC00274173-01

Molecular Formula: C₂₂H₃₆N₂O₄

Molecular Weight: 392.53224

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cis-adamantane-2-spiro-3’-8’-[[[(2’-amino-2’ methylpropyl) amino] carbonyl] methyl] 1’,2’,4’-trioxaspiro [4.5] decane

cis-adamantane-2-spiro-3′-8′-[[[(2′- amino-2′-methylpropyl)amino]carbonyl]-methyl]- 1 ‘,2′,4′-trioxaspiro[4.5]decane

Arterolane maleate is a synthetic trioxolane compound. The chemical name of arterolane maleate is cis-adamantane-2-spiro-3’-8’-[[[(2’-amino-2’ methylpropyl) amino] carbonyl] methyl] 1’,2’,4’-trioxaspiro [4.5] decane hydrogen maleate. The molecular formula is C26H40N2O8 and molecular weight is 508.61. The structural formula is as follows:

PATENT

http://www.google.st/patents/WO2007138435A2?cl=en

Example 6: Preparation of c/s-adamantane-2-spiro-3′ -8 ‘-πT(2′-amino-2′ -methyl propyl) amino! carbonyl] methyli-l ‘, 2\ 4′-U-JoXaSpJrQ [4.51 decane maleate To a solution of c/s-adamantane-2-spiro-3′-8′-[[[(2′-amino-2′-methyl propyl) amino] carbonyl] methyl]-! ‘, 2′, 4′-trioxaspiro [4.5] decane (example 5) (60 g, 0.153 moles) in ethanol (150 mL) was added a solution of maleic acid (17.3 g, 0.15 moles, 0.98 equiv. in ethanol 90 mL) and the reaction mixture was stirred for about 1 h. To this clear solution, n- heptane (720 mL) was added at room temperature in 1 h and the reaction mixture was stirred for 3 h. It was then cooled to 0 to 10⁰C and filtered. The cake was washed with n-heptane (60 mL) and dried under vacuum at 40-45⁰C.

Yield: 67 g, 77.4%,

mp: 149⁰C (decomp),

(M⁺+l) 393.5,

¹HNMR (300 MHz, DMSO-^ ): δ 1.05-1.11 (2H,m), 1.18 (6H,s), 1.64-1.89 (21H,m), 2.07(2H,d), 3.21 (2H,d), 6.06 (2H,d), 7.797 (2H, bs), 8.07 (IH, t).

SEE FULL ARTICLE WITH SYNTHESIS AT

http://newdrugapprovals.org/2014/12/18/ranbaxy-to-introduce-malarial-treatment-synriam-in-african-nations/

NMR PREDICTIONS

H-NMR spectral analysis