Perfluorophenyl 4-(nitrooxy)butanoate → HCID 178441677, compound

HRID 2241110Notes

Reaction equation

HRID 2241110 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].FC1C([O:38][C:39](=O)[CH2:40][CH2:41][CH2:42][O:43][N+:44]([O-:46])=[O:45])=C(F)C(F)=C(F)C=1F>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=3[C:26]3[NH:30][N:29]=[N:28][N:27]=3)=[CH:16][CH:15]=2)[C:7]([CH2:11][O:12][C:39]([CH2:40][CH2:41][CH2:42][O:43][N+:44]([O-:46])=[O:45])=[O:38])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 11522541Perfluorophenyl 4-(nitrooxy)butanoateHCID 178441684HCID 178441684, compound

Product 1

HCID 178441677HCID 178441677, compoundYield 67.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-butyl-4-chloro-1-[[2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol (0.48 g, 1.1 mmol), TEA (0.16 ml, 1.1 mmol) and DMAP (0.14 mg, 1.1 mmol) in DMF (3 ml), cooled to 0° C., a solution of 4-nitrooxybutyric acid pentafluorophenyl ester (0.36 g, 1.1 mmol) in DMF (3 ml) was added. The reaction was slowly warmed to room temperature and stirred for 3 hours. Then the solvent was evaporated under reduced pressure. The residue was dissolved in EtOAc (10 ml) and washed with a buffer solution (pH=3) then with brine. The organic layer was dried over Na2SO4, concentrated and purified by flash chromatography (CH2Cl2/MeOH 98:2) to afford the title compound (0.41 g, 66%).

Workup

  1. customThen the solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in EtOAc (10 ml)
  3. washwashed with a buffer solution (pH=3)
  4. dry with materialThe organic layer was dried over Na2SO4
  5. concentrationconcentrated
  6. custompurified by flash chromatography (CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-cedbdfb37e5143328c6a917d0ff44319
Source dataset
uspto-grants-2010_05
Patent number
US07723529B2

Reaction notes

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