1,3-Dibromopropane → HCID 117598924, compound

HRID 522399Notes

Reaction equation

HRID 522399 reaction equation
[C:1]([C@H:5]1[C:34](=[O:35])[N:33]2[CH2:36][C@@H:30]([CH2:31][C@H:32]2[C:37]([O:39][CH3:40])=[O:38])[O:29][C:17]2=[N:18][C:19]3[C:20]([O:27][CH3:28])=[CH:21][CH:22]=[CH:23][C:24]=3[C:25]([OH:26])=[C:16]2[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][C@@H:10]2[CH2:41][C@H:9]2[O:8][C:7](=[O:42])[NH:6]1)([CH3:4])([CH3:3])[CH3:2].[Br:43][CH2:44][CH2:45][CH2:46]Br.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Br:43][CH2:44][CH2:45][CH2:46][O:26][C:25]1[C:24]2[CH:23]=[CH:22][CH:21]=[C:20]([O:27][CH3:28])[C:19]=2[N:18]=[C:17]2[O:29][C@H:30]3[CH2:36][N:33]([C:34](=[O:35])[C@H:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[NH:6][C:7](=[O:42])[O:8][C@@H:9]4[CH2:41][C@H:10]4[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]=12)[C@H:32]([C:37]([O:39][CH3:40])=[O:38])[CH2:31]3

Participants

5

Reactant 3

HCID 80011,3-DibromopropaneHCID 10796Cesium carbonateHCID 178501307HCID 178501307, compound

Product 1

HCID 117598924HCID 117598924, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl (1aR,5S,8S,10R,22aR)-5-tert-butyl-17-hydroxy-13-methoxy-3,6-dioxo-1,1a,3,4,5,6,9,10,18,19,20,21,22,22a-tetradecahydro-8H-7,10-methanocyclopropa[18,19][1,10,3,6]dioxadiazacyclononadecino[11,12-b]quinoline-8-carboxylate (253 mg) (prepared by the same method as Example 113, Steps 1-5 with intermediates B10 and C8) and 1,3-dibromopropane (500 μl) in DMF (5 ml) was added cesium carbonate (700 mg). After 90 minutes of stirring at room temperature, the reaction mixture was partitioned between water/brine 1:1 and ethyl acetate. The product was extracted twice with ethyl acetate and the combined organic phases were washed with water and brine, dried over sodium sulfate and evaporated. The crude residue was purified by flash chromatography (ISCO 10%-50% ethyl acetate in hexanes) to afford a white solid (231 mg). LRMS (ES+) m/z 704.30 (M+H)+.

Workup

  1. customthe reaction mixture was partitioned between water/brine 1:1 and ethyl acetate
  2. extractionThe product was extracted twice with ethyl acetate
  3. washthe combined organic phases were washed with water and brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe crude residue was purified by flash chromatography (ISCO 10%-50% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-e07091c91b9041749473f79b3b819149
Source dataset
uspto-grants-2016_05
Patent number
US09328138B2

Reaction notes

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