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Ethylamine → HCID 53990869, Verbindung

HRID 1081283
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081283
[CH3:1][C:2]([NH:5][S:6]([C:9]1[S:17][C:16]2[S:15](=[O:19])(=[O:18])[NH:14][CH2:13][C:12](=O)[C:11]=2[CH:10]=1)(=[O:8])=[O:7])([CH3:4])[CH3:3].C([N:23]([CH2:26][CH3:27])[CH2:24][CH3:25])C.C1(C)C=CC(S(Cl)(=O)=[O:35])=CC=1.C(N)C.[CH2:42]1[CH2:46][O:45][CH2:44][CH2:43]1>>[CH2:44]([O:45][C:46](=[O:35])[CH2:42][CH2:12][CH2:13][N:14]1[CH2:27][C@H:26]([NH:23][CH2:24][CH3:25])[C:11]2[CH:10]=[C:9]([S:6]([NH:5][C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:7])=[O:8])[S:17][C:16]=2[S:15]1(=[O:18])=[O:19])[CH3:43]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 5

HCID 6341EthylamineHCID 73974-Toluenesulfonyl chlorideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 23363812HCID 23363812, Verbindung

Produkt 1

HCID 53990869HCID 53990869, VerbindungAusbeute 37,6 %

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

The product of Step A (8.50g, 19.07 mmol) was dissolved in THF (130 mL) and cooled to 0° C. Triethylamine (10.69 mL, 76.28 mmol) was added followed by p-toluenesulfonyl chloride. The mixture was stirred for three hours and an aqueous solution of ethylamine (20 mL) was added. The mixture was stirred overnight at room temperature and then evaporated to a residue which was diluted with ethyl acetate (100 mL). The ethyl acetate was separated, dried (MgSO4) and evaporated to provide a brown residue which was purified by column chromatography (silica, hexane-ethyl acetate gradient) to give 3.5 g (37.6%) of the desired compound as an oil.

Aufarbeitung

  1. stirringThe mixture was stirred overnight at room temperature
  2. customevaporated to a residue which
  3. additionwas diluted with ethyl acetate (100 mL)
  4. customThe ethyl acetate was separated
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. customto provide a brown residue which
  8. customwas purified by column chromatography (silica, hexane-ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-45f40a28d0d44f4185d5f8f36452df81
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05585377

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