1-(BOC-AMINO)-2-PROPANOL

Step 1: To a mixture of 1-amino-propan-2-ol (compound 42.1; 3.53 g, 47.0 mmol) and TEA (25 mL) in MeOH (35 mL) was slowly added a solution of di-tert-butyl dicarbonate (10.3 g, 47.0 mmol) in MeOH (15 mL). The resulting solution was stirred at room temperature over night. The mixture was then concentrated and the residue was dried under high-vacuum to yield 8.23 g (quantitative) of a clear oil. The oil thus obtained was dissolved in THF (100 mL) and treated with TEA (13.1 mL, 94.0 mmol). To the resulting solution was added methansulfonyl chloride (0.3.82 mL, 49.3 mmol) dropwise at 0° C. under nitrogen. After 1 hour, the mixture was diluted with EtOAc and washed with aqueous 1 M HCl, aq sodium bicarbonate, and brine. The organic phase was dried (NaTo a mixture of 1-aminopropan-2-ol (10.00 g, 133.14 mmol, 1.00 eq) in DCM, was added Boc2O (29.06 g, 133.14 mmol, 1.00 eq) in one portion at 30° C. under NInto a flask equipped with a magnetic stir bar the starting material 1-amino-2-propanol (I; 3.0 g, 60 mmol) was placed and it was dissolved in dry methanol (MeOH) (110 mL). The alkaline activator Et3N (16 mL) was added followed by slow addition of bis-tert-butyldicarbonate (60 mmol, 13.1 g) and the obtained reaction mixture was stirred under nitrogen for 30 minutes at 60°C. After completion of the reaction, methanol was evaporated under reduced pressure, the residue was diluted with water and then extracted with ethyl acetate (30 mL). The organic phase was washed with brine, dried over anhydrous Na2504 and the organic solvent was evaporated under reduced pressure. A colorless oily product (V-Boc, 6.8 g, 97percent yield) was obtained and characterized with ‘H, ‘3C NMR and IR analysis.53‘H NMR (500 MHz, CDCI3, ppm) 5.20 (bs, NH), 3.85 (m, 1H), 3.25 (m, 1H), 3.05 (bs, OH), 2.90 (m, 1H), 1.43 (s, 9H), 1.10 (d, J= 8 Hz, 3H);‘3C NMR (125 MHz, CDCI3, ppm) 157.0, 79.7, 67.6, 48.1, 28.5, 20.8;IR (neat): v = 3351 (broad, OH), 2975, 2931, 1684 (CO), 1514, 1365, 1248, 1167 cm’.1 g (13.3 mmol) of l-amino-propane-2-ol was dissolved in 40 mL of methanol and10 mL of water and then, 3.7 g (16.9 mmol) of di-t-butyl dicarbonate added thereto, followed by stirring for 3 hours at room temperature. To the solution, were added 200 mL of ethyl acetate and the reaction solution was washed with water, and then an organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, then the residue was purified by column chromatography to give 2.24 g (12.8 mmol) of the title compound in a yield of 96percent.[371] NMR: To a solution of 1-aminopropan-2-ol (44; 8.2 mL, 100 mmol) in THF-H2O (38 mL:38 mL) was added Boc2O (23 mL, 100 mmol) in THF (25mL). The mixture was stirred at 23 °C for 2 h and concentrated. Theorganic layer was extracted with EtOAc (2 × 100 mL). The combinedorganic layers were washed with aq NH4Cl (2 × 50 mL) and brine (100mL), dried (MgSO4), filtered, and concentrated to give 45 as a colorlessoil; yield: 16.0 g (92.0 mmol, 92percent).Example 20; Preparation of N-(1-(4Z, 7Z, 10Z, 13Z, 16Z, 19Z)-docosa-4, 7, 10, 13, 16, 19-hexaenamidopropan-2-yl)-2-hydroxybenzamide (13); To a solution of 1-aminopropan-2-ol (7.5 g, 0.1 mol) in THF-HBocTo a stirred solution of 1-aminopropan-2-ol (5 g, 66.6 mmol) in dichloromethane (50 mL), was added boc anhydride (17 mL, 79.92 mmol) and DIPEA (18 mL, 99.9 mmol), the reaction mixture was stirred at room temperature for about 1 h. To a stirred solution of 1-aminopropan-2-ol 59a (10 g, 133 mmol) in MeOH (360 mL) and HTo 1-amino-2-acetonitrile solution of propanol (0.973 g) (5 mL), 3 hours of stirring at room temperature by the addition of acetonitrile solution (6 mL) of di -tert- butyl (3.02 g) did. The reaction mixture was concentrated under reduced pressure, the resulting residue was purified by silica gel column chromatography (n- hexane / ethyl acetate) to give the title compound (2.9 g).In a 100 mL round bottom flask with nitrogen atmosphere 2.19 g (29.2 mmol) of 2-(methylamino)-ethanol are dissolved in 40 mL dry dichloromethane and cooled in an ice bath to 0 °C. 7.00 g (32.1 mmol) of di-tert-butylcarbonate are added to this solution and stirred overnight in the melting ice bath for 18 hours. Then the mixture is washed with 40 mL of 10percent citric acid in water and 40 mL of brine. Evaporation of the solvent in a rotavap yields 4.64 g of the title compound as an off-white solid (91percent).

Molecular Weight:175.23
XLogP3:0.7
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:175.12084340
Monoisotopic Mass:175.12084340
Topological Polar Surface Area:58.6
Heavy Atom Count:12
Complexity:151
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes