YU49474B - PROCEDURES FOR OBTAINING 2-β-D-RIBOFURANOSYLTHIAZOLE -4-CARBOXYLAMIDE - Google Patents
PROCEDURES FOR OBTAINING 2-β-D-RIBOFURANOSYLTHIAZOLE -4-CARBOXYLAMIDEInfo
- Publication number
- YU49474B YU49474B YU9695A YU9695A YU49474B YU 49474 B YU49474 B YU 49474B YU 9695 A YU9695 A YU 9695A YU 9695 A YU9695 A YU 9695A YU 49474 B YU49474 B YU 49474B
- Authority
- YU
- Yugoslavia
- Prior art keywords
- formula
- anhydro
- reaction
- ribofuranosylthiazole
- cooled
- Prior art date
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- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Postupak za dobijanje 2--D-ribofuranoziltiazol-4-karboksiamida formule I koji se odvija u pet faza, naznačen time, što se u fazi (a) reagovanjem 1-O-acetil-2,3,5-tri-O-benzoil- -D-ribofuranoze formule II, rastvorene u metilen-hloridu i rastvor ohlađen na 0 do 2В°C, sa trimetilsilil-cijanidom, u prisustvu kalaj(IV)-hlorida kao katalizatora, pri čemu se reakcija odvija na -5 do 0 В°C u toku 90 minuta, dobija 2,3-anhidro-3,4,6-tri-O-benzoil--D-alononitril (cijano šećer) formule III, posle čega se dobijeni cijano šećer, u fazi (b), u smeši sa metanolom i natrijum-metoksidom, na temperaturi od 35 do 45 В°C, uz mešanje u atmosferi azota u toku tri sata prevodi u metil-2,5-anhidro-D-alonimidat formule IV; a dobijeni alonimidat, u sledećoj fazi (c), u etanolu u prisustvu trietilamina ohlađen na 0В°C sa gasovitim vodonik-sulfidom na temperaturi -5 do 2 В°C, uz mešanje, daje 2,5-anhidro-D-alontioamid formule V, posel čega se reakcija odvija još jedan sat na sobnoj temperaturi, do potupnog izdvajanja proizvoda tioamida, koji se u fazi (d) kondenzuje sa etil-α-brom-piruvatom, u toku 10-14 časova, na sobnoj temperaturi u tetrahidrofuranu, pri čemu dolazi do stvaranja etil-2--D-ribofuranozil-tiazol-4-karboksilata formule VI, koji se dodaje, u poseldnjoj fazi (e), u rastvor metanola zasićenog amonijakom, i ohlađenim na -20В°C, da bi se posle stajanja na 4 do 8 В°C, u toku dva dana dobio proizvod 2--D-ribofuranoziltiazol-4-karboksamid formuel I. Prijava sadrži još 4 zavisna patentna zahteva.A process for the preparation of 2 - D-ribofuranosylthiazole-4-carboxamide of the formula I which takes place in five phases, characterized in that in step (a) the reaction of 1-O-acetyl-2,3,5-tri-O-benzoyl - -D-ribofuranose of formula II, dissolved in methylene chloride and the solution cooled to 0 to 2V ° C, with trimethylsilyl cyanide, in the presence of tin (IV) chloride as a catalyst, the reaction being carried out at -5 to 0 V At 90 [deg.] C., 2,3-anhydro-3,4,6-tri-O-benzoyl-D-alononitrile (cyano sugar) of formula III is obtained, after which cyano sugar is obtained, in step (b). in a mixture with methanol and sodium methoxide, at a temperature of from 35 to 45 V ° C, with stirring under a nitrogen atmosphere for three hours, it is converted to methyl-2,5-anhydro-D-alonimidate of formula IV; and the resulting anonimidate, in the next step (c), in ethanol in the presence of triethylamine cooled to 0V ° C with hydrogen sulphide gas at -5 to 2 V ° C, with stirring, yields 2,5-anhydro-D-allontioamide of the formula V, after which the reaction is continued for another hour at room temperature, until complete separation of the thioamide product, which is condensed in step (d) with ethyl α-bromo-pyruvate for 10-14 hours at room temperature in tetrahydrofuran. the formation of ethyl 2- D-ribofuranosyl-thiazole-4-carboxylate of formula VI, which is added, in the last step (e), to a solution of methanol saturated with ammonia, and cooled to -20V ° C, to after standing at 4 to 8 VC, within 2 days received the product 2 - D-ribofuranosylthiazole-4-carboxamide formula I. The application contains 4 more dependent claims.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU9695A YU49474B (en) | 1995-02-17 | 1995-02-17 | PROCEDURES FOR OBTAINING 2-β-D-RIBOFURANOSYLTHIAZOLE -4-CARBOXYLAMIDE |
| US08/603,106 US5907036A (en) | 1995-02-17 | 1996-02-20 | Procedures for obtaining ribo-C-nucleosides |
| PCT/US1996/002512 WO1996026212A1 (en) | 1995-02-17 | 1996-02-20 | Procedures for obtaining ribo-c-nucleosides |
| AU52980/96A AU5298096A (en) | 1995-02-17 | 1996-02-20 | Procedures for obtaining ribo-c-nucleosides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| YU9695A YU49474B (en) | 1995-02-17 | 1995-02-17 | PROCEDURES FOR OBTAINING 2-β-D-RIBOFURANOSYLTHIAZOLE -4-CARBOXYLAMIDE |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| YU9695A YU9695A (en) | 1997-12-05 |
| YU49474B true YU49474B (en) | 2006-05-25 |
Family
ID=47595144
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| YU9695A YU49474B (en) | 1995-02-17 | 1995-02-17 | PROCEDURES FOR OBTAINING 2-β-D-RIBOFURANOSYLTHIAZOLE -4-CARBOXYLAMIDE |
Country Status (1)
| Country | Link |
|---|---|
| YU (1) | YU49474B (en) |
-
1995
- 1995-02-17 YU YU9695A patent/YU49474B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| YU9695A (en) | 1997-12-05 |
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