NO132992B

• Main Authors: BEATTIE T R, CHRISTENSEN B G, LEANZA W J
• Format: Patent
• Language: English
• Published: 10.11.1975
• Subjects: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAININGELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN,SULFUR, SELENIUM OR TELLURIUM; CHEMISTRY; METALLURGY; ORGANIC CHEMISTRY

1,239,989. Diastereoisomeric salts of antipodes of (cis - 1,2 - epoxypropyl)phosphonic acid. MERCK & CO. Inc. 24 Oct., 1968 [30 Oct., 1967; 15 May, 1968; 20 Aug., 1968], No. 50638/68. Heading C2C. A diastereoisomeric salt of an antipode of (cis - 1,2 - epoxypropyl)phosphonic acid is obtained by reacting a mixture of such antipodes or a salt thereof with an optically active salt-forming compound, and separating and recovering the said diastereoisomeric salt. The optically active salt-forming compound is preferably an optically active base and may be used in an amount sufficient to form the optically active salts of one or both ( + ) and (-) enantiomers. When the salt of one enantiomer is formed the other enantiomer can be recovered from the mixture remaining after separation of the diastereoisomeric salt and when both salts are formed, one of the salts is first separated and the other salt is then recovered. The diastereoisomeric salts formed may be converted to the free (cis - 1,2 - epoxypropyl) phosphonic acid or to a different salt thereof, e.g. to an alkali metal- or alkaline earth metal salt. The process can also be carried out by reacting a mixture of the enantiomers with a mixture of an optically active base and an optically inactive salt-forming base and separating the optically active base salt of one of the enantiomers from the resulting reaction mixture, at least one-half mole of the optically active base being preferably used per mole of the enantiomers. In this procedure the two bases may be added to a solution of a mixture of the antipodes in a solvent and the optically active salt of one of the enantiomers separated from the reaction mixture. Thus the (+) - α - phenethyl - ammonium (-)(cis - 1,2 - epoxypropyl)phosphonate crystallizes from an aqueous solution of a mixture of (+) - α - phenethylamine and triethylamine salts of the racemic phosphonic salt. The optically active bases may be for example amines, hydrazines, imines, imino-esters, hydrazides, phosphines, biphosphines, phosphonium, stibonium or sulphonium compounds, stibines, arsines, alkaloids (e.g. (-) quinine), amino steroids or amino acids and several suitable bases are specified. Optically active allenes, spiranes, biphenyls, cycloalkenes and certain substituted ethanes may also be used as saltforming compounds. The diastereoisomeric salts can be separated by fractional crystallization from suitable solvents, especially C 1 -C 5 alkanols or aqueous C 1 -C 5 alkanols, or by chromatography or by the use of ureas, thioureas, or clathrates to form inclusion products with one of the diastereoisomeric salts.