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

HRID 2241109Notes

Reaction equation

HRID 2241109 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, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

Using the same procedure described in Example 1 but starting from 2-butyl-4-chloro-1-[[2′-(1H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol (Losartan)(2.13 g, 5.04 mmol) and 4-(nitrooxy)butanoic acid pentafluorophenyl ester (1.59 g, 5.04 mmol) TEA (0.7 ml, 5.04 mmol), DMAP (0.615 g, 5.04 mmol) and using DMF as solvent. Then the mixture was diluted with buffer solution (pH=3); the pH was adjusted to 2-3 and the mixture was extracted with EtOAc. The organic phase washed with brine, dried over Na2SO4 and evaporated. The residue was purified with Flash chromatography of the residue (CH2Cl2/MeOH 98:2) and the title compound was obtained as a white solid (1.48 g, 53%).

Workup

  1. extractionthe mixture was extracted with EtOAc
  2. washThe organic phase washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated
  5. customThe residue was purified with Flash chromatography of the residue (CH2Cl2/MeOH 98:2)

Sources & evidence

ORD record
ord-01e6a4a5804d48a0b9f5e8c18ef4dc8d
Source dataset
uspto-grants-2010_05
Patent number
US07723529B2

Reaction notes

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