N-Octylglucamine

white to light yellow crystal powde

An Preparation of N-(3-carboxy-l-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)- methylbutanoic acid ethyl ester n-Octyl-D-Glucamine salt. To a solution of N-(3-carboxy-l-oxopropyl)-(4S)-(p-phenylphenylmethyl)-4-amino-(2R)-methylbutanoic acid ethyl ester (25g) in acetone (250ml) was added n-Octyl-D-Glucamine (17.83g) under stirring at 10-15C. Reaction mixture was stirred for 5-10 minutes at 25-30C and then heated to reflux. At reflux temperature added water (5ml) in the reaction mixture. The reaction mixture was cooled to 10-20C and stirred at this temperature for 2-3 hours. Solid product was filtered and washed with acetone (50ml). After drying 35g (82%) product was obtained. The HPLC purity of the product is 99%.General procedure: To a solution of racemic acid 1 (5.68 mg, 0.04 mmol, 1 equiv) in IPA (0.2 mL, 0.2 M) was added the chiral base (0.04 mmol, 1 equiv as a 0.2 M stock solution in IPA). The resulting mixture was heated at 70 C for 15 min to solubilize all the solids, and then allowed to cool naturally to ambient temperature with stirring overnight. Overall, 23 precipitates were obtained from the 80 combinations. The enantiomeric excess of the solid precipitate and the liquor for each reaction was analyzed by SFC.Step IV- 5-methyl-(6S)-tetrahydrofolic acid and Step 111(a)- Preparation of Preparation of Example 5 - Synthesis of N-Octyl Acryloyl GlucamideN-Octyl GlucamineTo a 500ml round bottom flask was added N-Octyl Glucamine (5.00 g ), MEHQ (10 mg), Methanol (120ml), and triethyl Amine (3.80g). It was heated up to 60C under nitrogen, and with magnetic stirring. After all the solids were dissolved, the temperature was lowered to 50C. Acryloyl chloride (3.08g) in THF (20ml) was added dropwise. After 5 hrs reacting at 50C, TLC (15%Methanol/85%Ethyl Acetate) showed no starting N-Octyl Glucamine left. After vacuum evaporating of the solvents, lOg of solids were obtained; further purification was conducted with a column chromatography (Silica gel 60 (40-63 Microns available form EM Sciences, Gibbstown, NJ); 15% Methanol/85% Ethyl Acetate), and N-Octyl Acryloyl Glucamide (4.65 g white solid, 78.6% yield) was obtained. 1H NMR confirmed the structure depicted above was obtained.

1-Deoxy-1-(octylamino)-D-glucitol is used in the preparation of Dexketoprofen Trometamol.

Molecular Weight:293.40
XLogP3:0.1
Hydrogen Bond Donor Count:6
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:13
Exact Mass:293.22022309
Monoisotopic Mass:293.22022309
Topological Polar Surface Area:113
Heavy Atom Count:20
Complexity:218
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes