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The synthesis of 1-amino-2-hydroxy- and 2-amino-1-hydroxy-substituted ethylene-1,1-bisphosphonic acids and their N-methylated derivatives |
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| Authors: | D.V. Griffiths J.M. Hughes J.W. Brown J.C. Caesar S.P. Swetnam S.A. Cumming J.D. Kelly |
| Affiliation: | Department of Biological and Chemical Sciences, University of Essex, Colchester CO4 3SQ, U.K. Department of Chemistry, University of Keele, Staffordshire ST5 5BG, UK Amersham International p.l.c., Amersham, Buckinghamshire HP7 9LL, UK |
| Abstract: | A synthesis of 2-amino-1-hydroxyethylene-1,1-bisphosphonic acid 3 has been developed from N-phthaloylglycine via dimethyl 2-(N-phthaloylamino)acetylphosphonate 1. The preparation of the N-methylated and N,N-dimethylated derivatives 4 and 5 has been achieved by the reaction of 3 with formic acid and formaldehyde. The synthesis of 1-amino-2-hydroxyethylene-1,1-bisphosphonic acid 9 (R=R′=H) and its N-methylated and N,N-dimethylated analogues has been achieved by the reaction of phosphorus trichloride and phosphorous acid with the appropriate O-benzyl protected hydroxyacetamide, followed by catalytic hydrogenolysis of the protecting group. |
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