Compound 1
(S)-2-amino-3-(4-((bis(dimethylamino)phosphoryl)oxy)phenyl)propanoic acid
From: Site-specific incorporation of phosphotyrosine using an expanded genetic code
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Synthetic procedure: See article for the definitive version of this procedure and for full experimental details.
(S)-2-(((9H-fluoren-9-yl)methoxy)carbonylamino)-3-(4(bis(dimethylamino)phosphoryloxy) phenyl)propanoic acid (250 mg, 0.46 mmol) was dissolved in 3 mL 20% 4-methylpiperidine-DMF and stirred at r.t. for 20 min. Subsequently, the reaction mixture was added to cold Et2O (200 mL). The formed precipitate was removed and dried in vacuo to yield 120 mg (82%) of the final pure product 1. 1H-NMR (300 MHz, D2O) ppm: 7.12 (dd, J = 53.49, 8.25 Hz, 4H), 3.90-3.80 (m, 1H), 3.21-2.93 (m, 2H), 2.61 (d, J = 10.39 Hz, 12H); 13C-NMR (100 MHz, D2O) ppm: 173.749 (s), 149.500 (d) 132.055 (s), 130.881 (s), 120.900 (d), 55.906 (s), 35.711-35.615 (m). LC-ESI-MS m/z calculated for 1 (M+H)+: 316.13, found 316.27
