CA2130675A1 - Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor - Google Patents

Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Info

Publication number
CA2130675A1
CA2130675A1 CA002130675A CA2130675A CA2130675A1 CA 2130675 A1 CA2130675 A1 CA 2130675A1 CA 002130675 A CA002130675 A CA 002130675A CA 2130675 A CA2130675 A CA 2130675A CA 2130675 A1 CA2130675 A1 CA 2130675A1
Authority
CA
Canada
Prior art keywords
alkali metal
metal salt
phosphate
synthesis
enol ether
Prior art date
Legal status (The legal status 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 status listed.)
Granted
Application number
CA002130675A
Other languages
French (fr)
Other versions
CA2130675C (en
Inventor
Yrena Y. Bronstein
Brooks Edwards
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Applied Biosystems LLC
Original Assignee
Yrena Y. Bronstein
Brooks Edwards
Tropix, Inc.
Applera Corporation
Applied Biosystems Inc.
Applied Biosystems, Llc
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
Priority to US07/630,635 priority Critical patent/US5756770A/en
Priority claimed from US07/630,635 external-priority patent/US5756770A/en
Application filed by Yrena Y. Bronstein, Brooks Edwards, Tropix, Inc., Applera Corporation, Applied Biosystems Inc., Applied Biosystems, Llc filed Critical Yrena Y. Bronstein
Priority to CA002130675A priority patent/CA2130675C/en
Priority claimed from PCT/US1992/001530 external-priority patent/WO1993018022A1/en
Publication of CA2130675A1 publication Critical patent/CA2130675A1/en
Application granted granted Critical
Publication of CA2130675C publication Critical patent/CA2130675C/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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 System
    • 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
    • C07F9/6551—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 four-membered ring
    • C07F9/65512—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 four-membered ring condensed with carbocyclic rings or carbocyclic ring systems

Abstract

A novel synthesis of 1,2-dioxetane phosphate alkali metal salts and novel intermediates employed in this synthesis are dis-closed. A hydroxyaryl enol ether alkali metal salt having formula (1), wherein T can be an unsubstituted or substituted adamant-2'-ylidene group, R3 can be a methyl group, Y can be a phenyl group and M+ can be a sodium cation, is reacted with a phos-phorohalidate to give the corresponding enol ether ethylene phosphate, which is then reacted with an alkali metal cyanide to give the corresponding enol ether cyanoethyl phosphate diester alkali metal salt intermediate. Singlet oxygen addition to this enol ether cyanoethyl phosphate diester alkali metal salt intermediate to give the corresponding 1,2-dioxetane cyanoe-thyl phosphate diester alkali metal salt, followed by .beta.-elimination of the cyanoethyl group using an alkali metal hydroxide or the like, gives the corresponding 1,2-dioxetane phosphate alkali metal salt.
CA002130675A 1987-12-31 1992-03-05 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor Expired - Lifetime CA2130675C (en)

Priority Applications (2)

Application Number Priority Date Filing Date Title
US07/630,635 US5756770A (en) 1987-12-31 1990-12-20 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
CA002130675A CA2130675C (en) 1990-12-20 1992-03-05 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US07/630,635 US5756770A (en) 1987-12-31 1990-12-20 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
CA002130675A CA2130675C (en) 1990-12-20 1992-03-05 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor
PCT/US1992/001530 WO1993018022A1 (en) 1992-03-05 1992-03-05 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Publications (2)

Publication Number Publication Date
CA2130675A1 true CA2130675A1 (en) 1993-09-06
CA2130675C CA2130675C (en) 2003-06-10

Family

ID=27169831

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002130675A Expired - Lifetime CA2130675C (en) 1987-12-31 1992-03-05 Synthesis of stable, water-soluble chemiluminescent 1,2-dioxetanes and intermediates therefor

Country Status (1)

Country Link
CA (1) CA2130675C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112851709A (en) * 2019-11-26 2021-05-28 菲鹏生物股份有限公司 Synthesis process of AMPPD

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN112851709A (en) * 2019-11-26 2021-05-28 菲鹏生物股份有限公司 Synthesis process of AMPPD
CN112851709B (en) * 2019-11-26 2023-08-04 菲鹏生物股份有限公司 Synthetic process of AMPPD

Also Published As

Publication number Publication date
CA2130675C (en) 2003-06-10

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