Sodium hydride → HCID 86620260, compound

HRID 2238439Notes

Reaction equation

HRID 2238439 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 86620260HCID 86620260, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-74ccfbce6cce44a2904bff2198c95f77
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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