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CAS No. : | 1247119-36-3 | MDL No. : | MFCD28977898 |
Formula : | C21H34N4O8S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | QZLDJULECASEHV-NTISSMGPSA-N |
M.W : | 502.58 | Pubchem ID : | 73441912 |
Synonyms : |
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Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
122 g | Stage #1: With trimethylsilyl bromide In dichloromethane at 0 - 25℃; Stage #2: at 0 - 25℃; for 17 h; Stage #3: for 1 h; Reflux |
Example 6: Preparation of morpholine thiazole ethyl ester oxalate (salt Formula 2) A stirred mixture of (R)-(+)-a-amino-Y-butyrolactone hydrobromide (92 g) and dichloromethane (500 ml) was cooled to -5 to -8 °C. Carbonyl diimidazole (92 g) was then added to this mixture lot-wise. Triethylamine (45 g) was then added drop-wise with continued stirring until the starting material disappeared. 2-Isopropyl-4-[( - methylamino) methyl] thiazole di-hydrochloride (100 g) and triethylamine (92 g) were then slowly added to the mixture. The reaction mixture was stirred at about at 20-25°C for 15 hours. Water (200 ml) was added, and the organic layer was separated. The organic layer was washed with water (200 ml). The combined aqueous layers were back extracted with dichloromethane (100 ml). The collected the organic layers were then washed with 20percent aqueous citric acid solution (40 g). The combined organic layer was then washed with water (200 ml). The organic layer was concentrated under reduced pressure at about 38-40°C to obtain the crude urea N-methyl-N-[[2-(l-methylethyl)-4- thiazolyl]methyl]-N'-[(3S)-tetrahydro-2-oxo-3-furanyl] (80 g). The solution of urea N-methyl-N-[[2-(l-methylethyl)-4-thiazolyl]methyl]-N'-[(3S)- tetrahydro-2-oxo-3-furanyl] (100 g) dichloromethane (500 ml) was stirred at room temperature and ethanol (100 ml) was added. The reaction mass was cooled to 0-5 °C and trimethylsilyl bromide (183 g) was slowly added drop-wise. The reaction mass temperature was then raised to 19-25 °C and stirred until reaction was complete. The reaction mass was cooled to 0-5 °C and morpholine was added (230 g) drop wise slowly. The temperature was then raised to 19-25 °C and the reaction mass was stirred over a period of 17 hours. The reaction mixture was then filtered to remove morpholine hydrobromide salt. The filter cake was rinsed with dichloromethane. The filtrates were washed with water and the combined organic layer was concentrated under vacuum to dryness to give a residue. The residue was dissolved in acetone (500 ml). Oxalic acid dihydrate (60 g) in acetone (400 ml) was slowly added. The resulting slurry was refluxed for about one hour and cooled to 0-5 °C. The product was filtered and rinsed with acetone (200 ml) and dried under vacuum at 40°C to produce morpholine thiazole ethyl ester oxalate formula 2 as a white to off- white solid (122 g). |
52.5 g | Stage #1: With chloro-trimethyl-silane; sodium iodide In dichloromethane at 10 - 30℃; for 6 h; Inert atmosphere Stage #2: at 0 - 25℃; for 12 h; Stage #3: at 25 - 60℃; for 0.75 h; |
Sodium iodide (88.2 gm) was added to a mixture of (S)-i -((2-isopropylthiazol-4-yl)methyl)- 1 -methyl-3-(2-oxo- tetrahydrothran-3-yl)urea (50 gm), ethanol (60 ml) and dichloromethane (250 ml) at 25-30° C. under nitrogen atmosphere. Cooled the reaction mixture to 10-15° C. and trimethyl silyl chloride (70.3 gm) was slowly added to the reaction mixture at 10-15° C. Raised the temperature of the reaction mixture to 20-25° C. and stirred for 6 irs at the same temperature. Cooled the reaction mixture to 0-5° C. Morpholine (147 ml) was slowly added to the reaction mixture at 0-5° C. and temperature of the reaction mixture was raised to 20-25° C. Stirred the reaction mixture for 12 irs at 20-25° C. Water and dichioromethane were added to the reaction mixture and stirred for 30 minutes. Both the organic and aqueous layers were separated. Water was added to the organic layer and adjusted the pH of the reaction mixture to 6.0 with oxalic acid. Both the organic and aqueous layers were separated and organic layer was dried with sodium sulphate. Distilled off the solvent completely from the organic layer under reduced pressure and codistilled with acetone. Acetone (250 ml) was added to the obtained compound and stirred for 10 minutes at 25-30° C. A solution of Oxalic acid (30 gm) dissolved in acetone (200 ml) was added to the reaction mixture at 25-30° C. Heated the reaction mixture to 55-60° C. and stirred for 45 minutes at the same temperature. Cooled the reaction mixture to 25-30° C., further cooled to 0-5° C. and stirred the reaction mixture for 4 irs at 0-5° C. The obtained solid was filtered, washed with acetone. The obtained compound was recrystallized using acetone and dried to get the title compound. Yield: 52.5 gm; M.R.: 142-145° C. |
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