ChemicalBook CAS DataBase List (5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester

(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester synthesis

8synthesis methods

Product Name:(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester
CAS Number:149809-43-8
Molecular formula:C21H21F2N3O4S
Molecular Weight:449.47

98-59-9 Synthesis

98-59-9
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160709-02-4 Synthesis

D-threo-Pentitol, 2,5-anhydro-1,3,4-trideoxy-2-C-(2,4-difluorophenyl)-4-(hydroxyMethyl)-1-(1H-1,2,4-triazol-1-yl)-

160709-02-4
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(5R-cis)-Toluene-4-sulfonic acid 5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-yl)methyltetrahydrofuran-3-ylmethyl ester

149809-43-8
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$56.00/100mg

Yield:149809-43-8 215 g

Reaction Conditions:

with dmap in dichloromethane at 0 - 30; for 8.25 h;Reagent/catalyst;Solvent;

Steps:

12 Example-12: Preparation of ((3S,5R)-5-((1H-i,2,4-triazol-1-yl)methyl)-5-(2,4-difluoro phenyl) tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate (Formula-i)
Example-12: Preparation of ((3S,5R)-5-((1H-i,2,4-triazol-1-yl)methyl)-5-(2,4-difluoro phenyl) tetrahydrofuran-3-yl)methyl 4-methylbenzenesulfonate (Formula-i)Dimethyl aminopyridine (114 gins), followed by para toluene sulfonyl chloride (161 gins) were slowly added to a pre-cooled solution of dichioromethane (1250 ml) and ((3R,5R)-5-((1 H-i ,2,4-triazol- 1 -yl)methyl)-5-(2,4-difluorophenyl) tetrahydrofuran-3-yl)methanol (250 gins) at 0-5°C. Raised the temperature of the reaction mixture to 25-30°C and stirred for 8 hours at the same temperature. Water was added to the reaction mixture at 25-30°C and stirred for 15 minutes at the same temperature. Both the organic and aqueous layers were separated and washed the organic layer with 10% aqueous hydrochloric acid solution, followed by 10% aqueous sodiumcarbonate solution. Organic layer is washed with water. Distilled off the solvent from the organic layer and co-distilled with petroleum ether. Ethanol (1.00 ml) were added to the obtained solid at 25-30°C and heated to 60-65°C and then cooled to 25-30°C and stirred for 8 hrs at the same temperature. Further, cooled to 0-5 and filtered the precipitated solid, washed with ethanol and then dried to get the title compound. Yield: 215 gms. Purity by HPLC: 99.98%.

References:

MSN LABORATORIES PRIVATE LIMITED;THIRUMALAI RAJAN, Srinivasan;ESWARAIAH, Sajja;SAHADEVA REDDY, Maramreddy WO2015/59716, 2015, A2 Location in patent:Page/Page column 22