Trifluoromethanesulfonyl chloride → HCID 55256123, Verbindung

HRID 59712Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 59712
C(=O)(O)[O-].[Na+].[NH2:6][CH:7]([C:12]1[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=1)[CH2:8][C:9](O)=[O:10].FC(F)(F)S(Cl)(=O)=O>C(#N)C>[N:14]1[CH:15]=[CH:16][CH:17]=[C:12]([CH:7]2[NH:6][C:9](=[O:10])[CH2:8]2)[CH:13]=1

Komponenten

5

Edukt 3

HCID 79000Trifluoromethanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 36065473-Amino-3-(pyridin-3-yl)propanoic acid

Produkt 1

HCID 55256123HCID 55256123, VerbindungAusbeute 42 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
77.5 °C

Versuchsvorschrift

To a mixture of 20.20 g (0.24 mole) sodium bicarbonate (Sigma, Ultrapure, dried in good vacuum at room temperature for 3 days over phosphorus pentoxide) and 6.64 g (0.04 mole) 3-amino-3-(pyridine-3-yl)propionic acid (Tyger, dried in good vacuum at room temperature for 3 days over phosphorus pentoxide) under argon atmosphere first 200 ml of dry acetonitrile (Fisher) was added then at very strong stirring 4.7 ml (0.044 mole) trifluormethanesulfonyl chloride (Acros) was slowly added and thereafter the reaction mixture was further stirred in an oil bath of 75-80° C. for 19 hours. After cooling and stirring in ice bath for 1 hour the reaction mixture was filtered, washed three times with dry acetonitrile and the combined organic solutions were evaporated on a rotavapor at 35° C. The solid residue (23.8 g) was extracted in a Soxhlet-type extractor with boiling chloroform for 26 hours. The evaporation of the chloroform solution gave 2.48 g (42%) pure product as white crystalline material (mp: 115-116° C.).

Aufarbeitung

  1. additionwas added
  2. additionwas slowly added
  3. temperatureAfter cooling
  4. stirringstirring in ice bath for 1 hour the reaction mixture
  5. filtrationwas filtered
  6. washwashed three times with dry acetonitrile
  7. customthe combined organic solutions were evaporated on a rotavapor at 35° C
  8. extractionThe solid residue (23.8 g) was extracted in a Soxhlet-type extractor with boiling chloroform for 26 hours
  9. customThe evaporation of the chloroform solution

Quellen und Nachweise

ORD-Eintrag
ord-bbf56ee647a448dbb5b19014e52ea0bb
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440948B2

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