Perature 22 h, then the mixture was filtered and also the solvent was evaporated to provide a white residue. This residue was dispersed in 25 mL MeCN, the dispersion was transferred to stress bottle and cooled to -10 , followed by addition of trimethylamine (2 mL). The pressure bottle was sealed and heated to 65 for 48 h. Cooling to room temperature and after that with an ice-bath yielded a white precipitate, along with the acetonitrile phase was evaporated to offer an oily residue. The precipitate along with the oily residue have been purified on separate silica gel columns, packed with CHCl3/MeOH (4:1), and eluted with CHCl3/MeOH/H2O (65:25:four). Each columns yielded identical product 20 as a white solid (all round 0.211 g, 54 ). IR (CHCl3): 3340 br, 1728, 1656, 1210 cm-1; 1H NMR (CDCl3, 200 MHz) 0.83 (br t, 3H), 1.20 (br s, 32H), 1.52 (m, 2H), two.38 (s, 3H), two.94 (t, 2H, J = 7.4 Hz), three.ten (br s, 9H), three.20?.35 (m, 6H), three.72 (m, 2H), four.22 (m, 2H), 5.25 (m, 1H), six.17 (s, 1H), 7.08?.12 (m, 2H), 7.41 (d, 1H, J = eight Hz). 13C NMR (CDCl3, 50 MHz) 8.8, 14.3, 19.8, 22.8, 24.9, 27.1, 28.8, 29.0, 29.three, 29.five, 29.six, 29.7, 29.eight, 29.9, 32.1, 34.1, 39.six, 46.0, 54.5, 59.eight, 64.7, 65.1, 73.2, 113.8, 117.0, 123.0, 124.7, 144.0, 152.six, 154.0, 160.9, 167.7, 173.9, 173.7. 31P NMR (CDCl3, 160 MHz, pyrophosphate ref. ext.) -1.four br. Rf (CHCl3/MeOH/H2O 65:25:four) 0.45. Anal. Calcd for C40H67N2O9PS HCl3: C, 54.57; H, 7.60; N, three.10; Discovered: C, 54.84; H, 7.41; N, three.93. MS MH+ C40H67N2O9PSH Calcd: 783.4378, Found: 783.4331. []D20 -4.7?(c 1.11, CHCl3/MeOH four:1). 4.3.3. 3-(Dodecylamino)-3-oxo-2-[(tetrahydro-2H-pyran-2-yl)oxy]propyl phosphocholine (21)–To a option of 18 (0.Buy1471260-52-2 4462 g, 1.25 mmol) in 15 mL freshly distilled benzene, partially submerged in an ice-bath, was added 2-chloro-2-oxo-1,two,3dioxaphospholane (0.17 mL, 1.86 mmol) followed by a remedy of and triethylamine (0.26 mL, 1.86 mmol). Right after addition of NEt3, the ice-bath was removed and also the mixture was stirred for eight h at room temperature. The mixture was filtered and the residue collected was washed with benzene. The solvent was evaporated as well as the oily residue obtained was dissolved in 25 mL of CH3CN, the remedy was transferred to pressure bottle and frozen in a dry-ice bath at -10 . To this solid was added excess trimethylamine (five mL), then theNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTetrahedron. Author manuscript; offered in PMC 2015 Might 13.Rosseto and HajduPagepressure bottle was sealed, heated to 65 and kept for 60 h. Following 60 h, the stress bottle was cooled to space temperature, after which in an ice-bath. A white precipitate formed around the walls of pressure bottle. The solvent was evaporated, along with the residue in combination with all the precipitate was dissolved in CHCl3/MeOH/H2O (65:25:four) and loaded on a silica gel column packed together with the exact same solvent, and eluted with with CHCl3/MeOH/aq.Price of 117585-92-9 NH3 (1:9:1).PMID:33679749 The fractions containing the item have been collected, evaporated, dissolved in benzene and freeze-dried to offer 21 (0.4372 g, 67 ) as white strong. IR (CHCl3): 3312, 2852, 1672 cm-1; 1H NMR (CDCl3, 200 MHz) 0.86 (br t, 3H), 1.24 (br s, 18H), 1.52 (m, 6H), 1.77 (m, 2H), 3.10 (m, 2H), 3.36 (br s, 10H), 3.79 (m, 2H), three.95?.15 (m, 2H), 4.28 (m, 4H), 4.81 (m, 1H), 7.00 (m, 1H). 13C NMR (CDCl3, 50 MHz) 14.9, 17.3, 20.1, 22.6, 25.1, 27.four, 29.three, 29.6, 30.six, 31.8, 39.two, 52.9, 53.4, 55.eight, 59.7, 63.five, 67.2, 74.9, 100.0, 170.1. 31P NMR (CDCl3, 160 MHz, pyrophosphate ref. ext.) -0.62 Rf (CHCl3/MeOH/H2O 65:25:four) 0.25. Ana.