Sodium hydride → HCID 86620260, Verbindung

HRID 2238439Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2238439
[H-].[Na+].[Br:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:14]([N:17]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)(=[O:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6][C:5]=1[NH:32][C:33](=[O:39])[O:34][C:35]([CH3:38])([CH3:37])[CH3:36].[Cl:40][CH:41]=[CH:42][CH2:43]Cl>CN(C=O)C>[Br:3][C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([S:14]([N:17]([CH2:18][C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[CH2:25][C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)(=[O:16])=[O:15])[CH:12]=2)[CH:7]=[CH:6][C:5]=1[N:32]([CH2:43][CH:42]=[CH:41][Cl:40])[C:33](=[O:39])[O:34][C:35]([CH3:36])([CH3:38])[CH3:37]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 248831,3-DichloropropeneHCID 68691453HCID 68691453, Verbindung

Produkt 1

HCID 86620260HCID 86620260, VerbindungAusbeute 95 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

NaH (107 mg, 2.69 mmol, 60% in oil) was added to a solution of 212 (1.3 g, 2.24 mmol) in DMF (15 mL) at 0° C. 1,3-Dichloropropene (414 mg, 3.36 mmol, mixed isomers) was added and the mixture was allowed to warm to room temperature over 12 h. The DMF was evaporated under reduced pressure and the residue was partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, brine, then dried and evaporated. The residue was purified by chromatography on silica gel, eluting with petroleum ether/EtOAc (4:1) to give tert-butyl 1-bromo-7-[(dibenzylamino)sulfonyl]-2-naphthyl(3-chloro-2-propen-1-yl)carbamate (213) (1.39 g, 95%) as a yellow foam: 1H NMR (CDCl3) (mixture of rotamers and E and Z forms) δ 8.86 (s, 1H), 7.97-7.91 (m, 1H), 7.89-7.82 (m, 2H), 7.51-7.31, 7.26-7.16 (2 m, 7H), 7.13-7.06 (m, 4H), 6.14-6.01 (m, 2H), 4.64-4.48, 4.02-3.90 (2 m, 2H), 4.43 (s, 4H), 1.56, 1.33 (2 s, 9H). HRMS (FAB) calcd. for C32H3279Br35ClN2O4S (M) 655.1033, found 655.1032.

Aufarbeitung

  1. customThe DMF was evaporated under reduced pressure
  2. customthe residue was partitioned between EtOAc and H2O
  3. washThe EtOAc layer was washed with H2O, brine
  4. customdried
  5. customevaporated
  6. customThe residue was purified by chromatography on silica gel
  7. washeluting with petroleum ether/EtOAc (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-74ccfbce6cce44a2904bff2198c95f77
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07718688B2

Notizen zur Reaktion

Wird geladen…