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

HRID 561387

Reaktionsgleichung

Reaktionsgleichung von HRID 561387
[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.[CH3:12][C:13]1([CH3:21])[O:20][C:18](=[O:19])[CH2:17][C:15](=[O:16])[O:14]1.N1CCCC1C(O)=O.[CH3:30][S:31][CH2:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:41]=1[NH:40][CH:39]=[CH:38]2>C(#N)C>[S:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:38]3[C:37]4[C:41](=[C:33]([CH2:32][S:31][CH3:30])[CH:34]=[CH:35][CH:36]=4)[NH:40][CH:39]=3)[CH:17]3[C:18](=[O:19])[O:20][C:13]([CH3:21])([CH3:12])[O:14][C:15]3=[O:16])=[CH:9][C:4]=2[CH:3]=[CH:2]1

Komponenten

6

Edukt 4

HCID 614proline dl-formHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 139097Benzo(b)thiophene-5-carboxaldehydeHCID 583921877-[(Methylsulfanyl)methyl]-1H-indole

Produkt 1

HCID 583922775-[(1-Benzothiophen-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 (5.66 mmol) of 1-benzothiophene-5-carbaldehyde, 0.82 g (5.66 mmol) of Meldrum's acid and 0.03 g (0.28 mmol) of D,L-proline were added to a solution of 1.00 g (5.66 mmol) of the compound from Example 8A in 8 ml of acetonitrile. The reaction mixture was stirred at RT overnight and then the solvent was removed in vacuo. Purification of the residue by preparative HPLC (mobile phase: acetonitrile/water gradient) resulted in 1.73 g (71% purity, 47% of theory) of the title compound.

Aufarbeitung

  1. customthe solvent was removed in vacuo
  2. customPurification of the residue by preparative HPLC (mobile phase: acetonitrile/water gradient)

Quellen und Nachweise

ORD-Eintrag
ord-b2f5a39517734d4ca21c8fdca0d6e795
Quelldatensatz
uspto-grants-2011_11
Patentnummer
US08063234B2

Verknüpfte Notizen

Wird geladen…