Acetyl chloride → HCID 57675136, Verbindung

HRID 490918Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 490918
[C:1](Cl)(=[O:3])[CH3:2].Cl.[CH2:6]([N:8]1[C:12]2[N:13]=[CH:14][C:15]([C:24]3[O:28][N:27]=[C:26]([CH2:29][CH:30]4[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]4)[N:25]=3)=[C:16]([NH:17][CH:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[C:11]=2[CH:10]=[N:9]1)[CH3:7].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[C:1]([N:33]1[CH2:34][CH2:35][CH:30]([CH2:29][C:26]2[N:25]=[C:24]([C:15]3[CH:14]=[N:13][C:12]4[N:8]([CH2:6][CH3:7])[N:9]=[CH:10][C:11]=4[C:16]=3[NH:17][CH:18]3[CH2:19][CH2:20][O:21][CH2:22][CH2:23]3)[O:28][N:27]=2)[CH2:31][CH2:32]1)(=[O:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 6367Acetyl chloride2×HCID 81531Diisopropylethylamine2×HCID 67529443HCID 67529443, Verbindung

Produkt 1

HCID 57675136HCID 57675136, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

Acetyl chloride (0.04 mmol) was added to a stirred solution of Intermediate 125 (0.033 mmol) and diisopropylethylamine (0.1 mmol) in chloroform (1 ml) at room temperature. After stirring at room temperature for 1.5 h, a further quantity of acetyl chloride (0.04 mmol) and diisopropylethylamine (0.1 mmol) were added to the reaction mixture. After 3.5 h the reaction mixture was applied to a SPE cartridge (aminopropyl, 1 g) and the cartridge was eluted sequentially with chlororm, ethyl acetate and methanol. Fractions containing the desired product were combined and blown down under nitrogen. The resulting residue was further purified on a SPE cartridge (silica, 1 g) eluting with a gradient of 30-100% ethyl acetate in petroleum ether to afford Example 175 LCMS showed MH+=454, TRET=2.79 min.

Aufarbeitung

  1. waitAfter 3.5 h the reaction mixture was applied to a SPE cartridge (aminopropyl, 1 g)
  2. washthe cartridge was eluted sequentially with chlororm, ethyl acetate and methanol
  3. additionFractions containing the desired product
  4. customThe resulting residue was further purified on a SPE cartridge (silica, 1 g)
  5. washeluting with a gradient of 30-100% ethyl acetate in petroleum ether
  6. customto afford Example 175 LCMS
  7. customMH+=454, TRET=2.79 min.

Quellen und Nachweise

ORD-Eintrag
ord-6fdec317b5ed4a22aaaba2411eaf6456
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07528148B2

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