methyl (R)-alpha-t-butoxycarbonylamino-6,7-dichloro-3-dimethylphosphonomethyl-2-quinolinepropionate → (R)-alpha-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinolinepropanoic acid

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Reaction Steps

Methyl (R)-α-t-butoxycarbonylamino-6,7-dichloro-3-dimethylphosphonomethyl-2-quinolinepropionate (0.26 g, 0.5 mmol) was refluxed in 6M HCl (20 ml) for 4 h. The solvent was removed in vacuo and the residue was coevaporated 3 times with acetonitrile. The resulting powder was treated with water and chloroform, filtered off and finally recrystallized from methanol to give 0.11 g of (R)-α-amino-6,7-dichloro-3-(phosphonomethyl)-2-quinolinepropanoic acid. 1H NMR (D2O, 400 MHz): δ 3.15 (d,2H), 3.56 (dd,1H), 3.64 (dd,1H), 4.41 (m,1H), 7.91 (s,1H), 8.00 (s,1H), 8.02 (s,1H).

Provenance & Evidence