proline dl-form → 5-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 561388

Reaktionsgleichung

Reaktionsgleichung von HRID 561388
[CH3:1][C:2]1([CH3:10])[O:9][C:7](=[O:8])[CH2:6][C:4](=[O:5])[O:3]1.N1CCCC1C(O)=O.[Br:19][C:20]1[S:21][C:22]([CH:25]=O)=[CH:23][N:24]=1.[CH3:27][S:28][CH2:29][C:30]1[CH:31]=[CH:32][CH:33]=[C:34]2[C:38]=1[NH:37][CH:36]=[CH:35]2>C(#N)C>[Br:19][C:20]1[S:21][C:22]([CH:25]([C:35]2[C:34]3[C:38](=[C:30]([CH2:29][S:28][CH3:27])[CH:31]=[CH:32][CH:33]=3)[NH:37][CH:36]=2)[CH:6]2[C:7](=[O:8])[O:9][C:2]([CH3:10])([CH3:1])[O:3][C:4]2=[O:5])=[CH:23][N:24]=1

Komponenten

6

Edukt 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 27732592-Bromo-1,3-thiazole-5-carbaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Produkt 1

HCID 583922715-[(2-Bromo-1,3-thiazol-5-yl){7-[(methylsulfanyl)methyl]-1H-indol-3-yl}methyl]-2,2-dimethyl-1,3-dioxane-4,6-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

1.02 g (7.08 mmol) of Meldrum's acid, 0.04 g (0.34 mmol) of D,L-proline and 1.36 g (7.08 mmol) of 2-bromo-5-formylthiazole were successively added to a solution of 1.30 g (6.75 mmol) of the compound from Example 8A in 50 ml of acetonitrile. The reaction mixture was stirred at RT overnight and then the solvent was removed in vacuo. Purification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5) resulted in 3.58 g (81% purity, 87% of theory) of the title compound.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customPurification of the residue by flash chromatography on silica gel (mobile phase: dichloromethane/methanol 95/5)

Quellen und Nachweise

ORD-Eintrag
ord-f7633072c4254390973e72a6a89551ba
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

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