تفاعل #159552

معادلة التفاعل

N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamide

2-(2,6-difluorophenoxy)-5,5,6,6-tetramethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

N,N-diisopropylethylamine

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product

المردود 34.9%

2-(4-Fluorophenyl)-2-(5,5,6,6-tetramethyl-4,4-dioxo-5,6-dihydro-4H-4lambda6-[1,4,3]oxathiazin-2-ylamino)ethanesulfonamide

المردود 34.9%

المذيبات

dichloromethane

ethyl acetate

ظروف التفاعل

المعالجة

1. 1
   workup.STIRRINGthe mixture was stirred at room temperature overnight
2. 2
   غسيلwashed with 10 ml of 0.1 N hydrochloric acid and 10 ml of saturated aqueous sodium chloride solution
3. 3
   تجفيفThe organic phase was dried over MgSO4
4. 4
   تركيزconcentrated by rotary evaporation
5. 5
   workup.DISSOLUTIONThe residue was dissolved in 1 ml of trifluoroacetic acid
6. 6
   workup.DISSOLUTIONdissolved at room temperature for 20 hours
7. 7
   أخرىAfter the removal of the solvent under reduced pressure
8. 8
   أخرىthe crude product was purified in a purification laboratory by means of preparative HPLC

الإجراء التجريبي

50 mg of N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamide enantiomer 1 and 58 mg of 2-(2,6-difluorophenoxy)-5,5,6,6-tetramethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide were dissolved in 1 ml of dichloromethane, and the mixture was stirred at room temperature for 5 hours. The completeness of the conversion was checked by LCMS. Since no conversion had taken place yet, 60 μl of N,N-diisopropylethylamine were added and the mixture was stirred at room temperature overnight. The reaction solution was diluted with 20 ml of ethyl acetate and washed with 10 ml of 0.1 N hydrochloric acid and 10 ml of saturated aqueous sodium chloride solution. The organic phase was dried over MgSO4 and concentrated by rotary evaporation. The residue was dissolved in 1 ml of trifluoroacetic acid and dissolved at room temperature for 20 hours. After the removal of the solvent under reduced pressure, the crude product was purified in a purification laboratory by means of preparative HPLC. After lyophilization of the product-containing fractions, the product (25.8 mg) was obtained with a molecular weight of 407.5 g/mol (C15H22FN3O5S2); MS (ESI): m/e=408 (M+H+).

المصدر