Water → 3-[4-(2-Heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid

HRID 47813Notes

Reaction equation

HRID 47813 reaction equation
C([O:3][C:4](=[O:25])[C:5]([CH3:24])([CH3:23])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:9][CH:8]=1)C.B(Br)(Br)Br.O>C(Cl)Cl>[CH2:16]([NH:15][CH2:14][CH2:13][C:10]1[CH:9]=[CH:8][C:7]([CH2:6][C:5]([CH3:23])([CH3:24])[C:4]([OH:25])=[O:3])=[CH:12][CH:11]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]

Participants

5

Reactant 3

HCID 962WaterHCID 25134Boron tribromide2×HCID 69883898HCID 69883898, compound

Product 1

HCID 234312233-[4-(2-Heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of the impure 3-[4-(2-heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid ethyl ester (100 mg of the mixture) dissolved in methylene chloride (5 mL) cooled to −78° C. under a nitrogen atmosphere was added boron tribromide (1M in dichloromethane, 0.432 mL). The mixture was warmed to room temperature and stirred for 3 h. The mixture was cooled to −78° C. and an additional 0.432 mL of the 1M boron tribromide in dichloromethane was added. The mixture was warmed to room temperature and stirred for 20 minutes. The mixture was poured over H2O (10 mL) and extracted with dichloromethane (3×). The organic layers were combined, dried over anhydrous sodium sulfate, and concentrated to a clear film. This was dissolved in dioxane/2M HCl (10 mL/10 mL) and was refluxed for 20 minutes. The mixture was cooled and brought to pH 10 with 2 N NaOH. The basic solution was washed with diethyl ether (3×) and brought to pH 4 with 2N HCL. The acidic solution was extracted with diethyl ether (3×), washed with brine (2×), dried over anhydrous sodium sulfate and concentrated to give 3-[4-(2-heptylamino-ethyl)-phenyl]-2,2-dimethyl-propionic acid as a clear film (23 mg, 46%).

Workup

  1. temperatureThe mixture was warmed to room temperature
  2. temperatureThe mixture was cooled to −78° C.
  3. temperatureThe mixture was warmed to room temperature
  4. stirringstirred for 20 minutes
  5. extractionextracted with dichloromethane (3×)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated to a clear film
  8. dissolutionThis was dissolved in dioxane/2M HCl (10 mL/10 mL)
  9. temperaturewas refluxed for 20 minutes
  10. temperatureThe mixture was cooled
  11. washThe basic solution was washed with diethyl ether (3×)
  12. extractionThe acidic solution was extracted with diethyl ether (3×)
  13. washwashed with brine (2×)
  14. dry with materialdried over anhydrous sodium sulfate
  15. concentrationconcentrated

Sources & evidence

ORD record
ord-b75929fa69b14ec29f4afa3640ccb525
Source dataset
uspto-grants-2004_03
Patent number
US06699904B2

Reaction notes

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