Triethylamine → HCID 86617110, compound

HRID 1723698Notes

Reaction equation

HRID 1723698 reaction equation
[N:1]([C@@H:4]1[C@@H:8]([NH2:9])[CH2:7][N:6]([CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:5]1)=[N+:2]=[N-:3].[Br:17][CH2:18][C:19]([F:26])([F:25])[CH2:20][CH2:21][C:22](O)=[O:23].C(N(CC)CC)C>C(OCC)(=O)C>[N:1]([C@H:4]1[CH2:5][N:6]([CH2:10][C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH2:7][C@@H:8]1[NH:9][C:22](=[O:23])[CH2:21][CH2:20][C:19]([F:26])([F:25])[CH2:18][Br:17])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 57559193HCID 57559193, compoundHCID 86617109HCID 86617109, compound

Product 1

HCID 86617110HCID 86617110, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of the product from Step 5 (17.5 g, 80.6 mmol), 5-bromo-4,4-difluoropentanoic acid (17.5 g, 80.6 mmol) from Preparation 3 and triethylamine (32.6 g, 323 mmol) in ethyl acetate (250 mL) was added a 50% solution of propanephosphonic acid cyclic anhydride in ethyl acetate (48.0 mL, 80.6 mmol). The reaction was warmed to reflux and stirred for 16 hours. The reaction was cooled to room temperature and partitioned between ethyl acetate and H2O. The organic phase washed with saturated sodium carbonate solution and saturated sodium chloride solution and then dried over sodium sulfate and concentrated to provide 22.0 g (65%) of the product as an oil. MS m/z 416. (MH+).

Workup

  1. temperatureThe reaction was warmed
  2. temperatureto reflux
  3. custompartitioned between ethyl acetate and H2O
  4. washThe organic phase washed with saturated sodium carbonate solution and saturated sodium chloride solution
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-3ce4ab02cef14d34b2b3531ebc2d7be5
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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