Diisopropylethylamine → HCID 178431661, Verbindung

HRID 2369965Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2369965
C([NH:5][S:6]([CH2:9][CH:10]([NH2:18])[C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)(=[O:8])=[O:7])(C)(C)C.FC1C=CC=C(F)C=1O[C:23]1[O:24][C:25]([CH3:34])([CH3:33])[C:26]([CH3:32])([CH3:31])[S:27](=[O:30])(=[O:29])[N:28]=1.C(N(CC)C(C)C)(C)C>ClCCl.C(OCC)(=O)C>[F:17][C:14]1[CH:13]=[CH:12][C:11]([CH:10]([NH:18][C:23]2[O:24][C:25]([CH3:34])([CH3:33])[C:26]([CH3:32])([CH3:31])[S:27](=[O:30])(=[O:29])[N:28]=2)[CH2:9][S:6]([NH2:5])(=[O:7])=[O:8])=[CH:16][CH:15]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 68287917N-(tert-Butyl)-2-amino-2-(4-fluorophenyl)ethanesulfonamideHCID 867054542-(2,6-Difluorophenoxy)-5,5,6,6-tetramethyl-5,6-dihydro-1,4,3-oxathiazine 4,4-dioxide

Produkt 1

HCID 178431661HCID 178431661, VerbindungAusbeute 34,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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 (C15H22FN3O5S); MS (ESI): m/e=408 (M+H+).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. washwashed with 10 ml of 0.1 N hydrochloric acid and 10 ml of saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated by rotary evaporation
  5. dissolutionThe residue was dissolved in 1 ml of trifluoroacetic acid
  6. dissolutiondissolved at room temperature for 20 hours
  7. customAfter the removal of the solvent under reduced pressure
  8. customthe crude product was purified in a purification laboratory by means of preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b6e56c71811b40d6bc99cb1e08f4b218
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08710050B2

Notizen zur Reaktion

Wird geladen…