Sodium Iodide → tert-butyl(3S,4S)-1-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

HRID 1486045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1486045
[CH3:1][C@@H:2]1[N:8]([C:9](=[O:15])[CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])[C:7]2[CH:16]=[CH:17][CH:18]=[CH:19][C:6]=2[NH:5][C:4](=[O:20])[C@H:3]1[NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25].[Br:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[C:36]([CH2:40]Cl)=[C:35]([O:42][CH3:43])[CH:34]=[CH:33]2.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C=O)C.CCOC(C)=O>[Br:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][CH:39]=1)[C:36]([CH2:40][N:5]1[C:4](=[O:20])[C@@H:3]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[C@H:2]([CH3:1])[N:8]([C:9](=[O:15])[CH2:10][S:11]([CH3:14])(=[O:13])=[O:12])[C:7]3[CH:16]=[CH:17][CH:18]=[CH:19][C:6]1=3)=[C:35]([O:42][CH3:43])[CH:34]=[CH:33]2

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 7371226-Bromo-1-(chloromethyl)-2-methoxynaphthaleneHCID 131736772tert-butyl(2S,3S)-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate

Produkt 1

HCID 131736771tert-butyl(3S,4S)-1-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamateAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a rt solution of tert-butyl(2S,3S)-2-methyl-1-(2-(methylsulfonyl)acetyl)-4-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (60.3 mg, 147 μmol) in DMF (366 μl) was added 6-bromo-1-(chloromethyl)-2-methoxynaphthalene (50.2 mg, 176 μmol), cesium carbonate (62.1 mg, 191 μmol), and sodium iodide (28.6 mg, 191 μmol). The reaction was stirred at rt for 4 h, then diluted with EtOAc (30 mL), washed with H2O (30 mL) and sat. aq. NaCl (30 mL), dried over Na2SO4, filtered, and concentrated. The crude material was purified by flash chromatography to provide tert-butyl(3S,4S)-1-((6-bromo-2-methoxynaphthalen-1-yl)methyl)-4-methyl-5-(2-(methylsulfonyl)acetyl)-2-oxo-2,3,4,5-tetrahydro-1H-benzo[b][1,4]diazepin-3-ylcarbamate (75 mg, 78% yield) as a white solid. MS m/z 682/684 (MNa)+

Aufarbeitung

  1. washwashed with H2O (30 mL) and sat. aq. NaCl (30 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-262ca1caafa342f2b44152aa0e739fc1
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09422331B2

Notizen zur Reaktion

Wird geladen…