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Preparation of Diethyl 1-Phenyl-3-(4-methyl-3-oxo-3,6-dihydro-2
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-1,2-oxazin-2-yl)propylphosphonate (10b): A solution of 9b (1 g, 2.53 mmol) in anhyd CH2Cl2 (30 mL) was brought under a N2 atmosphere. The mixture was stirred at reflux temperature and Grubbs’ second-generation catalyst (0.1073 g, 0.126 mmol) was added. After 6 h of refluxing, the solvents were evaporated under vacuum to yield the product 10b as a crude oil. Purification by column chromatography was necessary to remove the traces of the ruthenium catalyst, yielding 10b (0.70 g, 1.90 mmol, 75%). 1H NMR (300 MHz, CDCl3): δ = 1.08 (t, J = 7.0 Hz, 3 H, OEt), 1.29 (t, J = 7.0 Hz, 3 H, OEt), 1.88 (q, J = 1.7 Hz, 3 H, CMe), 2.22-2.35 (m, 1 H, CHAHBCHP), 2.40-2.54 (m, 1 H, CHAHBCHP), 3.11 (ddd, J = 3.1, 11.2, 23.1 Hz, 1 H, CHP), 3.46 (ddd, J = 6.7, 6.8, 14.0 Hz, 1 H, CHAHBN), 3.59 (ddd, J = 7.2, 7.2, 14.0 Hz, 1 H, CHAHBN), 3.66-4.11 (m, 4 H, 2 × OEt), 4.35 (ddq, J = 1.7, 3.5, 15.4 Hz, 1 H, OCHAHBCH=C), 4.44 (ddq, J = 1.7, 3.5, 15.4 Hz, 1 H, OCHAHBCH=C), 6.35 (tq, J = 1.7, 3.5 Hz, 1 H, OCH2CH=C), 7.23-7.37 (m, 5 H, CHarom). 13C NMR (75 MHz, CDCl3, ref. CDCl3): δ = 15.70 (CMe), 16.27, 16.35, 16.45, 16.54 (2 × OEt), 27.78 (J
C-P = 2.3 Hz, CH2CHP), 42.33 (J
C-P = 138.5 Hz, CHP), 45.14 (J
C-P = 18.5 Hz, CH2N), 61.97 (J
C-P = 6.9 Hz, OEt), 62.81 (J
C-P = 6.9 Hz, OEt), 67.54 (OCH2CH=C), 77.13 (CDCl3), 127.44 (J
C-P = 2.3 Hz, CHarom), 128.67 (J
C-P = 2.3 Hz, 2 × CHarom), 129.40 (J
C-P = 6.9 Hz, 2 × CHarom), 129.67 (CMe), 132.92 (OCH2CH=C), 135.48 (J
C-P = 6.9 Hz, Cq,arom), 166.46 (CO). 31P NMR (109 MHz, CDCl3): δ = 28.92. IR (NaCl): 1674, 1635 (C=O, C=C), 1242 (P=O), 1058, 1028 (PO) cm-1. MS (ESI, +ve mode, %): m/z = 368.3 (100) [M + H+]. Chromatography (PE-EtOAc, 1:4): R
f
= 0.18.
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Preparation of Diammonium 1-Phenyl-3-(4-methyl-3-oxo-3,6-dihydro-2
H
-1,2-oxazin-2-yl)propylphos-phonate (1b): To a solution of 10b (0.50 g, 1.36 mmol) in anhyd MeCN at r.t. was added dropwise TMSBr (13.6 mmol) and this mixture was stirred at r.t. for 24 h. The solvents and traces of TMSBr were removed under reduced pressure and under high vacuum. The residual oil was dissolved in H2O and the pH was adjusted with a 5% NH4OH solution to pH 8-9. Lyophilization of the solution resulted in a solid and purification was performed by column chromatography on Whatman CF11 cellulose. The solvent used was MeCN-aq 1 M NH4OH (5:1) and the fractions were analyzed on cellulose TLC with the use of UV light to visualize the spots after dipping the plates in a pinacryptol yellow solution (0.1% in H2O) and drying with hot air. The desired fractions were again lyophilized, yielding 1b as a pale brown hygroscopic solid (0.31 g, 0.88 mmol, 65%). 1H NMR (300 MHz, CDCl3): δ = 1.72 (d, J = 1.7 Hz, 3 H, CMe), 2.14-2.42 (m, 2 H, CH2CHP), 2.93 (ddd, J = 3.0, 11.8, 22.0 Hz, 1 H, CHP), 3.50 (t, J = 6.5 Hz, 2 H, CH2N), 4.31 (ddd, J = 1.9, 3.6, 15.7 Hz, 1 H, OCHAHBCH=C), 4.44 (ddq, J = 1.9, 3.4, 15.7 Hz, 1 H, OCHAHBCH=C), 4.79 (D2O), 6.45 (tq, J = 1.7, 1.7 Hz, 1 H, OCH2CH=C), 7.19-7.35 (m, 5 H, 5 × CHarom). 13C NMR (75 MHz, CDCl3, ref. MeCN): δ = 1.47 (ref. MeCN), 15.20 (CMe), 28.13 (J
C-P = 2.3 Hz, CH2CHP), 44.79 (J
C-P = 129.2 Hz, CHP), 45.94 (J
C-P = 17.3 Hz, CH2N), 68.24 (OCH2CH=C), 119.69 (ref. MeCN), 127.17 (J
C-P = 2.3 Hz, CHarom), 128.36 (CMe), 129.00 (J
C-P = 2.3 Hz, 2 × CHarom), 129.69 (J
C-P = 6.9 Hz, 2 × CHarom), 135.26 (OCH2CH=C), 139.14 (J
C-P = 6.9 Hz, Cq,arom), 166.73 (CO). 31P NMR (109 MHz, CDCl3): δ = 22.91. IR (NaCl): 1668 (C=O, C=C), 1033 (PO) cm-1. MS (ESI, -ve mode, %): m/z = 310.3 (100) [M - +NH4 - NH3]. Chromatography (MeCN-1 M NH4OH, 5:1): R
f
= 0.16.