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CAS No. : | 224452-66-8 | MDL No. : | MFCD11045316 |
Formula : | C30H47NO4S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | STZYTFJPGGDRJD-FJJJPKKESA-N |
M.W : | 517.76 | Pubchem ID : | 6918462 |
Synonyms : |
SB-275833
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
91.2% | With potassium carbonate In acetone at 45℃; for 20 h; | Weigh TRP-THI 350.0g (1.81 mol), potassium carbonate 750.48g (5.43 mol), PLM-TS 1157.0g (2.17 mol) and dissolve in 1750 ml acetone. At 45 °C, react for 20 hours. TLC monitoring the reaction is complete, filtering, and then adding ethyl acetate filtrate turns on lathe does 1500 ml and 600 ml water, for 10percent hydrochloric acid to adjust the pH value to 6 - 7, separating the organic phase, then 1percent hydrochloric acid extraction of the organic phase, the aqueous phase is 10percent NaOH solution to adjust the pH value to 9 - 10, ethyl acetate (800 ml X3) extraction, turns on lathe does acetic acid ethyl ester, acetone for recrystallization to obtain the final product retapamulin 854.7g, yield 91.2percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
87.3% | With potassium carbonate In acetone at 50℃; for 12 h; | Weigh TRP-THI 120.5g (0.47 mol), potassium carbonate 196.26g (1.42 mol), PLM-TS 275.4g (0.52 mol) and dissolve in 600 ml in acetone. At 50 °C, react for 12 hours. TLC monitoring the reaction is complete, filtering, the filtrate after turns on lathe does adding ethyl acetate 500 ml and 300 ml water, for 10percent hydrochloric acid to adjust the pH value to 6 - 7, separating the organic phase, then 1percent hydrochloric acid extraction of the organic phase, the aqueous phase is 10percent NaOH solution to adjust the pH value to 9 - 10, ethyl acetate (300 ml X3) extraction, turns on lathe does acetic acid ethyl ester, anhydrous ethanol for recrystallization to obtain the final product retapamulin 212.44g, yield 87.3percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With triethylamine In 4-methyl-2-pentanone at 20 - 40℃; for 2 - 24 h; | Example 17 Preparation of Retapamulin A 3 neck-flask (100 ml) was charged with tropine thiol (5-10 mmol), a solvent (5 vol) and a base (2.5 eq). The solvents and bases are listed in Table 1 below. Pleuromutilin mesylate (11 mmol) was then added to the flask in portions. The resulting combination was stirred at room temperature to 40° C. for 2-24 hours until full conversion to Retapamulin was achieved. Example 18Preparation of RetapamulinIn a 500 ml round bottom flask, tropine thiol (15 g), methyl isobutyl ketone (8 vol) and triethylamine (2.4 eq.) were charged. The mixture was stirred at 40° C. for 15 minutes. Pleuromutilin mesylate (1 eq.) was added. The mixture was stirred as a slurry at 40° C. for 12 hours. Water (7 vol) was added and the pH was adjusted to 8.5 using 4N HCl. The phases were separated. Water (7 vol) was added to the organic phase, the pH was adjusted to 8.2, and the phases separated again. The organic phase was extracted with water (7 vol) and the pH was adjusted to 1.5. After separation, the pH of the aqueous phase was adjusted to 12.5 with 4N NaOH. The mixture was stirred at room temperature for 20 hours. The product was vacuum filtered and washed with water. The collected crystals were dried in a 55° C. vacuum oven to yield 80percent Retapamulin at 99.8percent purity as determined by HPLC. |
69.2% | at 30℃; for 2 h; Cooling with ice; Green chemistry | A solution of (1R, 3s, 5S) -8-methyl-8-azabicyclo [3.2.1] octane-3-thiol (6) obtained in Example 6 was added with pleuromutil mesylate 2(23.44 g, 51.38 mmol, 1 eq.),The mixture was cooled in an ice-water bath (internal temperature <30 ° C.) and 2 mol / L H2SO4 (90 ml, 359.66 mmol, 7 eq.) Was added dropwise thereto and reacted at 30 ° C. for 2 h. After the reaction was completed, the pH was adjusted with 2 mol / L HCl (25 ml, 1 eq.)≈8, EtOH (35 ) was evaporated under reduced pressure, water (280ml) and ethyl acetate (200ml) were added, mixed, separated and separated.The aqueous phase is extracted with ethyl acetate (150 ml + 50 ml).The organic phases were combined, washed with water (35ml), added with 4mol / L HCl (100ml) and stirred for 10min, allowed to stand, layered and separated.The organic phase was added 4mol / L HCl (100ml), stirred for 10min, allowed to stand, layered and separated.The organic phase was added with 4mol / L HCl (40ml), stirred for 10min, allowed to stand, layered and separated.Hydrochloric acid layers were combined and adjusted to pH 8 with 6 mol / L NaOH (200 ml) under ice-water bath and extracted with ethyl acetate (200 ml + 100 ml).The ethyl acetate layers were combined, washed with water (40 ml) and dried over anhydrous Na2SO4. The mixture was suction filtered and the ethyl acetate (40 ° C) was evaporated under reduced pressure to give 21.8 g of an off-white solid.Add EtOH / H2O (1: 1,110ml) heated to dissolve, the temperature was lowered to 50 ° C with stirring seed, cooled to room temperature and stirred (14h), precipitated a large amount of solid, suction filtered.The filter cake was washed with EtOH: H2O (1: 1, 15ml) and baked at 60 ° C for 6h to obtain 18.4g of white solid with a yield of 69.2percent |