IE32997L - Resolution of (cis-1, 2-epoxypropyl)-phosphonic acid - Google Patents

Resolution of (cis-1, 2-epoxypropyl)-phosphonic acid

Info

Publication number
IE32997L
IE32997L IE681252A IE125268A IE32997L IE 32997 L IE32997 L IE 32997L IE 681252 A IE681252 A IE 681252A IE 125268 A IE125268 A IE 125268A IE 32997 L IE32997 L IE 32997L
Authority
IE
Ireland
Prior art keywords
salt
optically active
salts
mixture
diastereoisomeric
Prior art date
Application number
IE681252A
Other versions
IE32997B1 (en
Original Assignee
Merck & Co Inc
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Merck & Co Inc filed Critical Merck & Co Inc
Publication of IE32997L publication Critical patent/IE32997L/en
Publication of IE32997B1 publication Critical patent/IE32997B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/655—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms
    • C07F9/65502—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having oxygen atoms, with or without sulfur, selenium, or tellurium atoms, as the only ring hetero atoms the oxygen atom being part of a three-membered ring
    • C07F9/65505—Phosphonic acids containing oxirane groups; esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/06—Phosphorus compounds without P—C bonds
    • C07F9/08—Esters of oxyacids of phosphorus
    • C07F9/09—Esters of phosphoric acids
    • C07F9/14—Esters of phosphoric acids containing P(=O)-halide groups
    • C07F9/1403—Esters of phosphoric acids containing P(=O)-halide groups containing the structure Hal-P(=O)-O-unsaturated acyclic group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
    • C07F9/6564—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms
    • C07F9/6571—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms
    • C07F9/657163—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom
    • C07F9/657181—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having phosphorus atoms, with or without nitrogen, oxygen, sulfur, selenium or tellurium atoms, as ring hetero atoms having phosphorus and oxygen atoms as the only ring hetero atoms the ring phosphorus atom being bound to at least one carbon atom the ring phosphorus atom and, at least, one ring oxygen atom being part of a (thio)phosphonic acid derivative

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Abstract

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. [GB1239989A]
IE1252/68A 1967-10-30 1968-10-21 Resolution of (cis-1,2-epoxypropyl)phosphonic acid and its optically-active forms IE32997B1 (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US67920367A 1967-10-30 1967-10-30
US72944568A 1968-05-15 1968-05-15
US75385868A 1968-08-20 1968-08-20

Publications (2)

Publication Number Publication Date
IE32997L true IE32997L (en) 1969-04-30
IE32997B1 IE32997B1 (en) 1974-02-20

Family

ID=27418346

Family Applications (1)

Application Number Title Priority Date Filing Date
IE1252/68A IE32997B1 (en) 1967-10-30 1968-10-21 Resolution of (cis-1,2-epoxypropyl)phosphonic acid and its optically-active forms

Country Status (17)

Country Link
BE (1) BE723073A (en)
CH (1) CH527224A (en)
DE (1) DE1805681C3 (en)
DK (1) DK139141B (en)
ES (1) ES359542A1 (en)
FI (1) FI51703C (en)
FR (1) FR1592150A (en)
GB (1) GB1239989A (en)
IE (1) IE32997B1 (en)
IL (1) IL30920A (en)
IT (1) IT986758B (en)
LU (1) LU57184A1 (en)
NL (1) NL6814979A (en)
NO (1) NO132992C (en)
OA (1) OA03882A (en)
RO (1) RO54819A (en)
SE (1) SE377941B (en)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IT1161974B (en) * 1978-02-02 1987-03-18 Italchemi Spa CIS.I 2 EPOXYPROPYLPHOSPHONIC ACID DERIVATIVES THEIR PREPARATION PROCEDURE AND PHARMACEUTICAL COMPOSITIONS CONTAINING THEM
DE3906953A1 (en) * 1989-03-04 1990-09-20 Byk Gulden Lomberg Chem Fab METHOD FOR PRODUCING OPTICALLY PURE OXIRANCARBONIC ACIDS
JP2988631B2 (en) 1989-07-12 1999-12-13 塩野義製薬株式会社 Lyophilized preparation of fosfomycin sodium and method for producing the same
CN109369718A (en) * 2018-12-07 2019-02-22 武汉工程大学 A kind of preparation method of left phosphorus dexammonium salt and fosfomycin
EP4678176A1 (en) * 2024-07-11 2026-01-14 Ercros, S.A. Amino acid salts of fosfomycin and compositions thereof

Also Published As

Publication number Publication date
SE377941B (en) 1975-08-04
IL30920A (en) 1973-03-30
LU57184A1 (en) 1969-05-16
FI51703C (en) 1977-03-10
IT986758B (en) 1975-01-30
CH527224A (en) 1972-08-31
DE1805681A1 (en) 1969-12-11
DE1805681B2 (en) 1974-02-14
RO54819A (en) 1973-02-17
NO132992C (en) 1976-02-18
BE723073A (en) 1969-04-29
ES359542A1 (en) 1970-10-16
DK139141B (en) 1978-12-27
FR1592150A (en) 1970-05-11
NO132992B (en) 1975-11-10
IL30920A0 (en) 1968-12-26
IE32997B1 (en) 1974-02-20
FI51703B (en) 1976-11-30
OA03882A (en) 1975-08-14
DE1805681C3 (en) 1974-09-19
DK139141C (en) 1979-05-28
NL6814979A (en) 1969-05-02
GB1239989A (en) 1971-07-21

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