1-Methylimidazole → (S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-4-oxo-4-phenylbutanamide

HRID 509136

Reaktionsgleichung

Reaktionsgleichung von HRID 509136
[C:1]([CH2:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN1C=CN=C1.S(Cl)(Cl)=O.[CH2:24]([C:26]1[N:27]=[C:28]([C@@H:31]([NH2:42])[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)[S:29][CH:30]=1)[CH3:25]>C(Cl)Cl>[CH2:24]([C:26]1[N:27]=[C:28]([C@@H:31]([NH:42][C:11](=[O:13])[CH2:10][CH2:9][C:1](=[O:8])[C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:32][C:33]2[CH:38]=[CH:37][C:36]([N+:39]([O-:41])=[O:40])=[CH:35][CH:34]=2)[S:29][CH:30]=1)[CH3:25]

Komponenten

6

Edukt 4

HCID 13901-MethylimidazoleHCID 24386Thionyl ChlorideHCID 728713-Benzoylpropionic acidHCID 57943187(S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine

Produkt 1

HCID 59464671(S)-N-[1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethyl]-4-oxo-4-phenylbutanamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

3-Benzoylpropionic acid (0.250 g) is dissolved in CH2Cl2 (5 mL), N-methyl imidazole (0.333 mL) is added and the resulting solution is cooled to 0° C. after which a solution of thionyl chloride (0.320 g) in CH2Cl2 (2 mL) is added dropwise. After 0.5 hours (S)-1-(4-ethylthiazol-2-yl)-2-(4-nitrophenyl)ethanamine, 3, (0.388 g) is added. The reaction is stirred for 18 hours at room temperature and then concentrated in vacuo. The resulting residue is dissolved in EtOAc and washed with 1N HCl and brine. The solution is dried over Na2SO4, filtered, and concentrated and the crude material purified over silica to afford 0.415 g of the desired product.

Aufarbeitung

  1. additionis added dropwise
  2. concentrationconcentrated in vacuo
  3. dissolutionThe resulting residue is dissolved in EtOAc
  4. washwashed with 1N HCl and brine
  5. dry with materialThe solution is dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customthe crude material purified over silica

Quellen und Nachweise

ORD-Eintrag
ord-ff49d2f1be53475c8f3970b1bcfafb0e
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096555B2

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