GB950290A - Improvements in or relating to a process for the preparation of heterocyclic phosporic acid amides - Google Patents
Improvements in or relating to a process for the preparation of heterocyclic phosporic acid amidesInfo
- Publication number
- GB950290A GB950290A GB38800/60A GB3880060A GB950290A GB 950290 A GB950290 A GB 950290A GB 38800/60 A GB38800/60 A GB 38800/60A GB 3880060 A GB3880060 A GB 3880060A GB 950290 A GB950290 A GB 950290A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbonyl
- phosphoric acid
- heterocyclic
- mono
- esters
- 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.)
- Expired
Links
- 125000000623 heterocyclic group Chemical group 0.000 title abstract 5
- 150000001408 amides Chemical class 0.000 title 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 9
- -1 Heterocyclic phosphoric acid amides Chemical class 0.000 abstract 8
- 235000011007 phosphoric acid Nutrition 0.000 abstract 5
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N 4-methylimidazole Chemical compound CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 abstract 2
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 150000005690 diesters Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 2
- QWUWMCYKGHVNAV-UHFFFAOYSA-N 1,2-dihydrostilbene Chemical group C=1C=CC=CC=1CCC1=CC=CC=C1 QWUWMCYKGHVNAV-UHFFFAOYSA-N 0.000 abstract 1
- CMTBLAIURUVTEP-UHFFFAOYSA-N CC(C)C1=CC=C(C)C=C1OP(O)(O)=O.C1=CN=CN1 Chemical class CC(C)C1=CC=C(C)C=C1OP(O)(O)=O.C1=CN=CN1 CMTBLAIURUVTEP-UHFFFAOYSA-N 0.000 abstract 1
- ASMQGLCHMVWBQR-UHFFFAOYSA-N Diphenyl phosphate Chemical compound C=1C=CC=CC=1OP(=O)(O)OC1=CC=CC=C1 ASMQGLCHMVWBQR-UHFFFAOYSA-N 0.000 abstract 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 1
- OIRDTQYFTABQOQ-KQYNXXCUSA-N adenosine group Chemical group [C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=NC=2C(N)=NC=NC12 OIRDTQYFTABQOQ-KQYNXXCUSA-N 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000008064 anhydrides Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 125000006267 biphenyl group Chemical group 0.000 abstract 1
- PGPAMLREPDTQCG-UHFFFAOYSA-N bis(1,2,3-triphenylimidazol-2-yl)methanone Chemical compound C(=O)(C1(N(C=CN1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1)C1(N(C=CN1C1=CC=CC=C1)C1=CC=CC=C1)C1=CC=CC=C1 PGPAMLREPDTQCG-UHFFFAOYSA-N 0.000 abstract 1
- VRAVWQUXPCWGSU-UHFFFAOYSA-N bis(1h-1,2,4-triazol-5-yl)methanone Chemical compound N1=CNN=C1C(=O)C=1N=CNN=1 VRAVWQUXPCWGSU-UHFFFAOYSA-N 0.000 abstract 1
- OJKZEZMAPKWHTG-UHFFFAOYSA-N bis(2h-triazol-4-yl)methanone Chemical compound C=1NN=NC=1C(=O)C1=CNN=N1 OJKZEZMAPKWHTG-UHFFFAOYSA-N 0.000 abstract 1
- DUYAPABVVRDPSP-UHFFFAOYSA-N bis(3,5-dimethyl-1H-pyrazol-4-yl)methanone Chemical compound C(=O)(C=1C(=NNC1C)C)C=1C(=NNC1C)C DUYAPABVVRDPSP-UHFFFAOYSA-N 0.000 abstract 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract 1
- PFKFTWBEEFSNDU-UHFFFAOYSA-N carbonyldiimidazole Chemical compound C1=CN=CN1C(=O)N1C=CN=C1 PFKFTWBEEFSNDU-UHFFFAOYSA-N 0.000 abstract 1
- 150000001735 carboxylic acids Chemical class 0.000 abstract 1
- 239000005515 coenzyme Substances 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 1
- ANCLJVISBRWUTR-UHFFFAOYSA-N diaminophosphinic acid Chemical compound NP(N)(O)=O ANCLJVISBRWUTR-UHFFFAOYSA-N 0.000 abstract 1
- YQHVEGTZGGQQMV-UHFFFAOYSA-N dicyclohexyl hydrogen phosphate Chemical class C1CCCCC1OP(=O)(O)OC1CCCCC1 YQHVEGTZGGQQMV-UHFFFAOYSA-N 0.000 abstract 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract 1
- 235000011180 diphosphates Nutrition 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- 150000003948 formamides Chemical class 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 1
- 125000003835 nucleoside group Chemical group 0.000 abstract 1
- 150000007530 organic bases Chemical class 0.000 abstract 1
- 238000010647 peptide synthesis reaction Methods 0.000 abstract 1
- 150000003014 phosphoric acid esters Chemical class 0.000 abstract 1
- 238000003786 synthesis reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
- C07H1/02—Phosphorylation
-
- 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
- C07F9/645—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having two nitrogen atoms as the only ring hetero atoms
- C07F9/6503—Five-membered rings
- C07F9/6506—Five-membered rings having the nitrogen atoms in positions 1 and 3
-
- 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
- C07F9/6558—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system
- C07F9/65583—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom containing at least two different or differently substituted hetero rings neither condensed among themselves nor condensed with a common carbocyclic ring or ring system each of the hetero rings containing nitrogen as ring hetero atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07K—PEPTIDES
- C07K1/00—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length
- C07K1/06—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents
- C07K1/08—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents
- C07K1/082—General methods for the preparation of peptides, i.e. processes for the organic chemical preparation of peptides or proteins of any length using protecting groups or activating agents using activating agents containing phosphorus
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Genetics & Genomics (AREA)
- Engineering & Computer Science (AREA)
- Biotechnology (AREA)
- Analytical Chemistry (AREA)
- Biophysics (AREA)
- Medicinal Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Saccharide Compounds (AREA)
Abstract
Heterocyclic phosphoric acid amides are obtained by reacting an NN1-carbonyl diheterocyclic compound wherein each heterocyclic ring is five membered, unsaturated, substituted or unsubstituted, and has at least two nitrogen atoms incorporated therein, with orthophosphoric acid or its mono- or di-esters. Specified N,N1-carbonyl compounds are carbonyl-diimidazole, carbonyl-di(4- or 5-methyl imidazole), carbonyl-di (triphenyl imidazole), carbonyl-di-(1, 2, 3-triazole), carbonyl-di-(1, 2, 4-triazole), carbonyl - dibenzimidazole, carbonyldibenz-1, 2, 3-triazole and carbonyl-di (3, 5-dimethyl pyrazole). Specified phosphoric acid esters are mono- and di-phenyl phosphoric acid and their nuclear substituted derivatives, naphthyl phosphoric acid and its nuclear substituted derivatives, and benzyl-, p-nitrobenzyl-, cyclohexyl, adenosine-, dibenzyl, di-p-nitrophenyl-, diethyl and dicyclohexyl phosphoric acids. When orthophosphoric acid or its monoesters are used the heterocyclic monoamide first formed may be reacted with a second molecule of the N, N1-carbonyl compound to form a heterocyclic phosphoric acid diamide. The reaction may be exemplified by the following scheme.: <FORM:0950290/C2/1> wherein R1 and R2 which may be the same or different are hydrogen, or an alkyl, aralkyl, aryl, cycloalkyl or nucleoside group. The above referred to diamide products have the formula: <FORM:0950290/C2/2> wherein N represents the heterocyclic ring as defined above. The products in which at least one of R1 and R2 is a hydrogen atom may be suitably isolated in the form of their organic base or alkali metal salts and may be reacted with alcohols to form esters, with amines to form amides, or with carboxylic acids to form anhydrides which are useful in the peptide synthesis; also they may be reacted with phosphoric acid or its mono- or di-esters to form pyrophosphates which reaction may be applied in the synthesis of coenzymes. Examples are given for the production of diphenyl-, monophenyl-, monobenzyl-, p-chloro-phenyl-, betanaphthyl-, monomethyl glycol-, and monothymyl-phosphoric acid mono-imidazolides and ortho-phosphoric acid mono- and di-imidazolides.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DES65826A DE1113937B (en) | 1959-11-13 | 1959-11-13 | Process for the preparation of heterocyclic amides of phosphoric acid |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB950290A true GB950290A (en) | 1964-02-26 |
Family
ID=7498334
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB38800/60A Expired GB950290A (en) | 1959-11-13 | 1960-11-11 | Improvements in or relating to a process for the preparation of heterocyclic phosporic acid amides |
Country Status (2)
| Country | Link |
|---|---|
| DE (1) | DE1113937B (en) |
| GB (1) | GB950290A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1159052A (en) * | 1980-02-29 | 1983-12-20 | University Patents, Inc. | Process for making oligonucleotides |
-
1959
- 1959-11-13 DE DES65826A patent/DE1113937B/en active Pending
-
1960
- 1960-11-11 GB GB38800/60A patent/GB950290A/en not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DE1113937B (en) | 1961-09-21 |
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