3-(benzyloxycarbonylamino)-N-(2-bromoethyl)propionamide → 3-(Benzyloxycarbonylamino)-N-[2-(benzoylthio)ethyl]propionamide

HRID 1583507

Reaktionsgleichung

Reaktionsgleichung von HRID 1583507
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18]Br)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([O-:28])(=[S:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[K+]>CC(C)=O>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]([NH:16][CH2:17][CH2:18][S:27][C:20](=[O:28])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:15])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

4

Edukt 2

HCID 202587523-(benzyloxycarbonylamino)-N-(2-bromoethyl)propionamideHCID 23681850Potassium thiobenzoate

Produkt 1

HCID 134919943-(Benzyloxycarbonylamino)-N-[2-(benzoylthio)ethyl]propionamideAusbeute 68,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel2×

Versuchsvorschrift

To the solution of 3-(benzyloxycarbonylamino)-N-(2-bromoethyl)propionamide (10.0 g, 0.03 mol) in acetone (250 ml), acetone (100 ml) solution of potassium thiobenzoate (5.35 g, 0.03 mol) is added. The mixture is stirred for 1 hour and insoluble substance is filtered off. The filtrate is concentrated in vacuo and the residue is dissolved in chloroform. The solution is washed with sodium hydroxide solution, water and then saturated sodium chloride solution, and dried over anhydrous magnesium sulfate. The solution is concentrated in vacuo to give 7.9 g (68%) of the titled compound.

Aufarbeitung

  1. filtrationinsoluble substance is filtered off
  2. concentrationThe filtrate is concentrated in vacuo
  3. dissolutionthe residue is dissolved in chloroform
  4. washThe solution is washed with sodium hydroxide solution, water
  5. dry with materialsaturated sodium chloride solution, and dried over anhydrous magnesium sulfate
  6. concentrationThe solution is concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-9ed9e6b582544b2db1b97b798496dd4c
Quelldatensatz
uspto-grants-1985_11
Patentnummer
US04552765

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