Carbonate Ion → HCID 18668628, compound

HRID 1059255Notes

Reaction equation

HRID 1059255 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]([OH:41])([C:17]2[N:18]=[CH:19][N:20]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:21]=2)[CH:14]([CH3:16])[CH3:15])=[CH:9][C:8]=1[C:42]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=1)(=O)=O.[C:51](=[NH:64])([C:58]1[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=1)[C:52]1[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1.C(=O)([O-])[O-]>C1(C)C=CC=CC=1>[C:52]1([C:51](=[N:64][C:7]2[C:8]([C:42]3[CH:43]=[CH:44][C:45]([F:48])=[CH:46][CH:47]=3)=[CH:9][C:10]([C:13]([C:17]3[N:18]=[CH:19][N:20]([C:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)([C:35]4[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[CH:21]=3)([OH:41])[CH:14]([CH3:15])[CH3:16])=[CH:11][CH:12]=2)[C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=1

Participants

5

Reactant 3

HCID 19660Carbonate IonHCID 136809Benzophenone imineHCID 18668561HCID 18668561, compound

Product 1

HCID 18668628HCID 18668628, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 4′-fluoro-5-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl][1,1′-biphenyl]-2-yl trifluoromethanesulfonate (1.06 g), benzophenone imine (0.035 ml) and cecium carbonate (1.23 g) in toluene (15 ml) were added (RS)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (56.4 mg) and tri(dibenzylideneacetone)dipalladium(0) (27.7 mg), and the mixture was stirred at 80-90° C. for 26 h. (RS)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (112 mg) and tri(dibenzylideneacetone)palladium(0) (55.4 mg) were further added, and the mixture was stirred at 80-90° C. for 16.5 h, and at 105° C. for 3.5 h. The reaction mixture was filtered through Celite, and the filtrate was washed with water and saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel chomatography (eluent; hexane:ethyl acetate=5:1→1:1) to give the yellow amorphous title compound (115 mg).

Workup

  1. additionwere further added
  2. waitat 105° C. for 3.5 h
  3. filtrationThe reaction mixture was filtered through Celite
  4. washthe filtrate was washed with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe residue was purified by silica gel chomatography (eluent; hexane:ethyl acetate=5:1→1:1)

Sources & evidence

ORD record
ord-96bb037cf100440e83282d96fd509286
Source dataset
uspto-grants-2003_02
Patent number
US06518257B1

Reaction notes

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