4-Toluenesulfonyl chloride → N-(p-toluenesulphonyl)-L-alanyl-L-proline ethylamide

HRID 47048

Reaktionsgleichung

Reaktionsgleichung von HRID 47048
Br.[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH2:13])[CH3:3].[C:17]1([CH3:27])[CH:22]=[CH:21][C:20]([S:23](Cl)(=[O:25])=[O:24])=[CH:19][CH:18]=1>N1C=CC=CC=1>[CH2:2]([NH:4][C:5](=[O:16])[C@@H:6]1[CH2:10][CH2:9][CH2:8][N:7]1[C:11](=[O:15])[C@H:12]([CH3:14])[NH:13][S:23]([C:20]1[CH:21]=[CH:22][C:17]([CH3:27])=[CH:18][CH:19]=1)(=[O:25])=[O:24])[CH3:3]

Komponenten

4

Edukt 2

HCID 73974-Toluenesulfonyl chlorideHCID 70602162L-alanyl-L-proline ethylamide hydrobromide

Produkt 1

HCID 53646160N-(p-toluenesulphonyl)-L-alanyl-L-proline ethylamideAusbeute 33 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

1.0 g (0.0033 mol) of L-alanyl-L-proline ethylamide hydrobromide was dissolved in 20 ml of dry pyridine and 0.63 g (0.0033 mol) of p-toluenesulphonyl chloride was added. The mixture was stirred at room temperature for 1 hour and the pyridine was then removed by evaporation. The oily residue was dissolved in chloroform and the solution was washed with water, dried over magnesium sulphate and evaporated to an oil. This oil was dissolved in water and freeze-dried to yield 0.40 g (33%) of N-(p-toluenesulphonyl)-L-alanyl-L-proline ethylamide; [α]D20 =-90.7° (c=0.94% in water).

Aufarbeitung

  1. customthe pyridine was then removed by evaporation
  2. dissolutionThe oily residue was dissolved in chloroform
  3. washthe solution was washed with water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to an oil
  6. dissolutionThis oil was dissolved in water
  7. customfreeze-dried

Quellen und Nachweise

ORD-Eintrag
ord-bc8d1b97509e42f6b38d35bbc920ab0f
Quelldatensatz
uspto-grants-1979_11
Patentnummer
US04176116

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