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Ethanol → 1-[3-(4-Bromobenzoyl)-3-benzoylthiopropionyl]-L-proline

HRID 903447
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 903447
[H-].[Na+].C(O)(=[S:10])C1C=CC=CC=1.[CH2:12]([OH:14])[CH3:13].[Br:15][C:16]1[CH:36]=[CH:35][C:19]([C:20]([CH:22](Br)[CH2:23][C:24]([N:26]2[CH2:33][CH2:32][CH2:31][C@H:27]2[C:28]([OH:30])=[O:29])=O)=[O:21])=[CH:18][CH:17]=1.C(OCC)(=O)C.[CH3:43][CH2:44][CH2:45][CH2:46][CH2:47]C.C(O)(=O)C>>[Br:15][C:16]1[CH:36]=[CH:35][C:19]([C:20]([CH:22]([C:12](=[O:14])[C:13]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[CH2:23][C:24]([N:26]2[CH2:33][CH2:32][CH2:31][C@H:27]2[C:28]([OH:30])=[O:29])=[S:10])=[O:21])=[CH:18][CH:17]=1
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Komponenten

6

Edukt 5

HCID 702EthanolHCID 24758Sodium hydrideHCID 21901998Ethyl acetate hexane acetic acidHCID 539233931-[3-(4-Bromobenzoyl)-3-bromopropionyl]-L-prolineHCID 178526132HCID 178526132, Verbindung

Produkt 1

HCID 537685831-[3-(4-Bromobenzoyl)-3-benzoylthiopropionyl]-L-proline

Versuchsvorschrift

To 440 mg. of sodium hydride in oil dispersion is added a solution of 1.60 g. of thiobenzoic acid in 25 ml. of ethanol. The mixture is stirred for 30 minutes and then 4.33 g. of 1-[3-(4-bromobenzoyl)-3-bromopropionyl]-L-proline (Example 37) is added and the mixture is stirred at room temperature for 18 hours, the solvent is removed in vacuo and the residue is partitioned between dichloromethane and water. The organic layer is washed with water, then sodium chloride solution, dried over magnesium sulfate and evaporated to dryness in vacuo leaving a peach colored glass. A 2.8 g. portion of this glass is dissolved in ethyl acetate-hexane-acetic acid (75:25:2) and placed on a 1"×15" column of silica gel. The column is eluted with the same solvent system (100 ml. hold back volume) taking 50 ml. cuts. The desired product is recovered in cut number 2 as a glass.

Aufarbeitung

  1. stirringthe mixture is stirred at room temperature for 18 hours
  2. customthe solvent is removed in vacuo
  3. customthe residue is partitioned between dichloromethane and water
  4. washThe organic layer is washed with water
  5. dry with materialsodium chloride solution, dried over magnesium sulfate
  6. customevaporated to dryness in vacuo
  7. customleaving a peach colored glass
  8. washThe column is eluted with the same solvent system (100 ml. hold back volume)
  9. customThe desired product is recovered in cut number 2 as a glass

Quellen und Nachweise

ORD-Eintrag
ord-e1fc875b80ed4f8e80208f478136e812
Quelldatensatz
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04226775

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