25 mL MeCN, the dispersion was transferred to stress bottle and cooled to -10 , followed by addition of trimethylamine (two mL). The stress bottle was sealed and heated to 65 for 48 h. Cooling to area temperature after which with an ice-bath yielded a white precipitate, plus the acetonitrile phase was evaporated to give an oily residue. The precipitate plus the oily residue had been purified on separate silica gel columns, packed with CHCl3/MeOH (4:1), and eluted with CHCl3/MeOH/H2O (65:25:4). Each columns yielded identical product 20 as a white solid (overall 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), 2.38 (s, 3H), two.94 (t, 2H, J = 7.4 Hz), 3.ten (br s, 9H), 3.20.35 (m, 6H), three.72 (m, 2H), four.22 (m, 2H), 5.25 (m, 1H), 6.17 (s, 1H), 7.08.12 (m, 2H), 7.41 (d, 1H, J = eight Hz). 13C NMR (CDCl3, 50 MHz) eight.eight, 14.3, 19.eight, 22.8, 24.9, 27.1, 28.8, 29.0, 29.3, 29.5, 29.6, 29.7, 29.eight, 29.9, 32.1, 34.1, 39.6, 46.0, 54.5, 59.eight, 64.7, 65.1, 73.two, 113.8, 117.0, 123.0, 124.7, 144.0, 152.6, 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, 3.ten; Discovered: C, 54.84; H, 7.41; N, 3.93. MS MH+ C40H67N2O9PSH Calcd: 783.4378, Discovered: 783.4331. []D20 -4.7(c 1.11, CHCl3/MeOH 4:1). four.three.three. 3-(Dodecylamino)-3-oxo-2-[(tetrahydro-2H-pyran-2-yl)oxy]propyl phosphocholine (21)–To a answer of 18 (0.4462 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.Teclistamab 17 mL, 1.86 mmol) followed by a option of and triethylamine (0.26 mL, 1.86 mmol). Right after addition of NEt3, the ice-bath was removed as well as the mixture was stirred for 8 h at room temperature. The mixture was filtered plus 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 option was transferred to stress bottle and frozen within a dry-ice bath at -10 .1,2-Distearoyl-sn-glycero-3-phosphorylcholine To this solid was added excess trimethylamine (five mL), then theNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTetrahedron.PMID:23892407 Author manuscript; obtainable in PMC 2015 May 13.Rosseto and HajduPagepressure bottle was sealed, heated to 65 and kept for 60 h. Right after 60 h, the stress bottle was cooled to room temperature, then in an ice-bath. A white precipitate formed around the walls of pressure bottle. The solvent was evaporated, and the residue in mixture using the precipitate was dissolved in CHCl3/MeOH/H2O (65:25:four) and loaded on a silica gel column packed using the exact same solvent, and eluted with with CHCl3/MeOH/aq.NH3 (1:9:1). The fractions containing the product were collected, evaporated, dissolved in benzene and freeze-dried to give 21 (0.4372 g, 67 ) as white solid. 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), three.ten (m, 2H), 3.36 (br s, 10H), 3.79 (m, 2H), 3.95.15 (m, 2H), 4.28 (m, 4H), four.81 (m, 1H), 7.00 (m, 1H). 13C NMR (CDCl3, 50 MHz) 14.9, 17.3, 20.1, 22.six, 25.1, 27.4, 29.three, 29.6, 30.six, 31.eight, 39.2, 52.9, 53.4, 55.8, 59.7, 63.five, 67.two, 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. Anal. Calcd for C25H51N2O7P 2O: C, 55.54; H, 9.88; N, 5.18; Found: C, 55.18; H, 9.83; N, five.14. MS MH+ C25H51N2O7PH+ Calcd: 523.3512, Located.